References - Springer978-1-4613-2651-9/1 · References for Chapter 2 405 42. T. Mitsuyasu and J....

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H. B. Jonassen and A. Weiddberger, Interscience, New York (1968); W. L. Jolly, The Synthesis and Characterization of Inorganic Compounds, Prentice-Hall, Englewood, Cliffs, New Jersey (1970).

34. D. F. Shriver, The Manipulation of Air-Sensitive Compounds, McGraw-HilI, New York (1969).

Subject Index

Acetals, to ethers, 300 Acetylacetonates, 390 Acetylenic alcohols, hydrogenation of, 278 Active-methylene compounds

alkylation of propargyl complex by, 30 telomerization with 1,3-dienes, 25

Acylaminoacrylic acids, asymmetric hydrogenation of, 330

Acyl anion equivalents, in conjugate addition, 56,57

Acyl halides to acyl dienes, 256 from a1kenes and CCI 4 , 245 from alkyl halides, 195, 197, 199 from allyl halides, 244 decarbonylation of, 260-263 reaction with 4-trimethylsilylbut-I-ene, 76

Adams' catalyst (Pt02), 379, 380, 387; see also platinum catalysts

Adiponitrile, from butadiene, 4 Air-sensitive compounds, handling of, 397 Alcohols

acetylenic, to tetrahydropyranones, 164 from aldehydes and ketones, 300, 309 aIkylamino, 348 a1lylic, 47,251

epoxidation of, 354 isomerization to retones, 181

to carboxylic acids, 196, 199,200,361,370 to esters, 212, 232 homoallylic, to a-methylene lactones, 161 to ketones, 47, 181, 362 telomerization with 1,3-dienes, 25

431

Alcohols (cont.) to a,~-unsaturated aldehydes, 363

Aldehydes from acyl halides, 310 from alcohols, 361 from alkanes, 356 from a1kenes, 4, 247-252, 358 to a1kenes, 62-64 from a1lylic alcohols, 47, 363 from amines, 366 to amino acids, 211 from anhydrides, 312 to carboxylic acids, 371 decarbonylation of, 260-263 from halides, 246, 247 hydrogenation of, 300, 301 from imines, 323 preferential reduction of, 307, 308 to pyrans, 163 to a-siloxyaldehydes, 253

Aldehydic acids, from anhydrides, 312 Alkanes

to alcohols, 344 to aldehydes and ketones, 356 from a1kenes, 53, 58, 279 from a1kynes, 274 from aromatics, 291

Alkenes to acyl chlorides, 245 from aldehydes, 260-262 to aldehydes, 347-352, 358 from a1kenylboranes, 18 from a1kynes, 15, 274

432

Alkenes (cant.) from 1T-allyl complexes, 14 to 1T-allyl complexes, 19, 20 to amides, 236-238 amination of, 142 arylation of, 15,45-48 to bis(siloxy)alkenes, 253 from carbonyl compounds, 62-64 to carboxylic acids, 205-2 II , 370 codimerization of, 5 cyclic cooligomerization of, 79, 80, 89, 94,

110, 130 cyclodimerization, II3 cyclopropanation of, 70 cyclotrimerization of, 78 from vic-dihalides, 62-64 dimerization of, 10-12 to I, 3-dioxans, 163 epoxidation of, 351 from epoxides, 58, 64, 65 to esters, 220-227 hydrocarboxylation of, 205-211 hydroesterification of, 220 hydroformylation of, 174, 347-352 hydrozirconation of, 16, 174, 175,206,224 industrial processes using, 4, 5 isomerization of, 173-193 to ketones, 249, 255-258 metathesis of, 58-61 nucleophilic attack on, 9 polymerization of, 23, 24, 61 preparation of, 10-30 from silyl enol ethers, 14 vicinal oxyamination of, 348

Alkenylalanes to aryl alkenes, 15, 16 to dienes, 28

Alkenylboranes alkyl transfer in, 18 cross-coupling of, 18, 28

Alkenyl cuprates

from alkynes, 18 alkylation of, 18, 19

Alkenyl halides, 26, see also vinyl halides Alkenyl pentaf!uorosilicates, to dienes, 29 Alkenyl zirconium complexes

alkylation of, 17 from alkynes, 15 arylation of, 16 vinylation of, 18

Alkyl alkynes, 31 Alkyl arenes

from aryl halides, 41, 42 via ortho-metallation, 44, 45

Subject Index

Alkyl copper compounds, in conjugate addition, 53-58

Alkyl halides to aldehydes, 246 to alkyl alkenes, 28 allylation of, 14 carbonylation of, 197, 199 to carboxylic acids, 203, 219 to esters, 219 to ketones, 254, 256

Alkynes addition of allylic halides to, 29 addition of organocuprates to, 18 addition to a,~-unsaturated ketones, 32 to aminopyridines, 155 arylation and alkylation of, 31, 43 to but-2-enolides, 161 to carboxylic acids, 210-212 cyclic cooligomerization of, 84, 95, llO,

ll6, 131, 135 cyclopropenation of, 75 cyclotetramerization of, 127 cyclotrimerization of, 85, 105, 107 to dienes, 29 to esters and lactones, 226-232 hydroalumination of, 15, 28 hydroboration of, 18 hydrocarboxylation of, 210-212 hydrometallation of, 15 hydrozirconation of, 16, 28 to ketones, 257-258, 360 from propargyl complex, 30 to pyridines, 154 reaction with organoalanes, 16, 17

Alkynyl alanes, conjugate addition of, 32 Alkynyl zinc reagents

to aryl alkynes, 31 to dienes, 30

Allenic acids, 210 Allyl acetates, 340 Allyl alcohols

epoxidation of, 354 to ketones, 47, 181 to a,~-unsaturated aldehydes, 363 to a,~-unsaturated ketones, 309

Allyl amides, to enamides, 183

Subject Index

Allyl amines, to enamines, 182 Allylation, protection by, 182 'IT-Allyl complexes

alkylation of, 20-23 allylation of halides by, 14, 19, 20, 26, 27 diene trimerization by, 24 from enones, 20 telomerization by, 25, 26

Allyl dibromides, coupling of, 136 Allyl dithiocarbamates, in cross-coupling, 27 Allyl ethers, 179, 180 Allyl halides

to acyl halides, 244 to carboxylic acids, 209, 211 to esters, 230 to lactones, 231, 232

Allylic alkylation, 18, 19-23 Amides

and aldehydes, to amino acids, 211 from alkenes, 236-238 from amines, 233, 234 decarbonylation of, 262 from halides, 234, 235

Amines to aldehydes and ketones, 366 allenic, cyclization of, 145 to amides, 233, 235 from formamides, 262 to lactams, 235-239 from nitriles, 320, 322 from nitro-compounds, 313 telomerization with 1,3-dienes, 25

Amino acids, N-acyl, 211 Amino alkynes, fromnitroalkynes, 274, 317 J3-Amino esters, from keten silyl acetals,

143 Anhydrides

from alkynes, 243 from diazonium salts, 204, 243 from esters and ethers, 213, 241-243

Anilines alkene arylation by, 48 artha-allyl, cyclization of, 149 artho-bromo-N-acryloyl,

to oxindoles, 146 to quinolines, 154

artha-chloro-N-allyl, to indoles, 150 from cyclohexeneimines, 193 to quinazolines, 168

Annulation, of arenes, 40, 41

Arenes 2-alkenyl-I-alkynyl, cyclization of, 102 alkylation of, 44 'IT-complexes of, 33-41, 391 hydrogenation of,S, 291-300

Arylalkenes from a1kenes, 45-48 cycloaddition to dibromoketones, 90

Arylalkynes, from aryl halides, 31 Aryl copper compounds

arylation of halides by, 43 biaryls from, 52 conjugate addition by, 43 polynuclear, 51, 52

Aryl halides to aldehydes, 247 allylation of, 14 to amides, 234, 235 from aroyl halides, 261 to arylalkenes, 45-48 to arylalkynes, 43 to carboxylic acids, 201-204 cross-coupling of, 6, 31,41-43 cyanation of, 42 to esters, 214-219 hydrogenolysis of, 338 to lactams, 235 to lactones, 216-219

Arylmethylenechroman-4-ones, 187 Asymmetric allylic alkylation, 21, 23 Asymmetric hydrogenation, 325-328 Axial alcohols, from cyclic ketones, 303 Aziridines

from alkenes, 142 to N-carboxynortropidines, 150

Azirines to isocyanates, 260 to pyrroles, 148 to styryl indoles, 148

Azobenzenes artha-alkylation of, 45 to heterocycles, 166 from nitroarenes, 315

Benzoazepinones, 157 Benzocyclobutenes, 85, 108 Benzo-2-furanones, 162

433

Benzoic acids, 2-alkenyl, to isocoumarins, 164 I ,4-Benzoxazines, 170 Benzyl alcohols, hydrogenolysis of, 339

434

Benzylamines, ortho-alkylation of, 45 Benzyl halides

to amides, 234 to arylacetic acids, 202, 203 to benzylalkynes, 18, 19

Biaryls from arenes, 38,48, 50 from arenesulfinic acids, 50 by coupling, 50-52 by cross-coupling, 49, 50 from diaryl cuprates, 52, 53

Bipyridines, from cyanopyridines, 6, 155 Bromohydrins, to alkenes, 65 Butenolides

from alkynes, 161 hydroxy-, 231, 232 from iodoallyl alcohols, 218 a-methylene-, 231 from vinyl mercury compounds, 233

Carbamates, 349 Carbanions

alkylation by, 9, 20-23 arylation of, 35-37, 41, 43 Michael 'reaction of, 53 stabilization of, 33

Carbenes from diazoacetates, 71 from gem-dihaloalkanes, 70

Carbenium ions in Koch carboxylic acid synthesis, 199 stabilization of, 34

Carbonylation, and decarbonylation, 195-263 Carbonyls, metal, 392, 393 Carboxylic acids

from alcohols, 199,200,361,370 from aldehydes, 211, 271 from alkanes, 207, 208 from alkenes, 205-211, 370 from alkynes, 210-212 from halides, 20 I telomerization with I, 3-dienes, 25

Catalysts, preparation of, 379-390 Catechols, oxidative cleavage of, 369 Chemical suppliers, list of, 378 Chiral cross-coupling, 13 Claisen rearrangement, 181 Clemmensen reduction, 301 Cobalt cyclopentadienyls

to thiophenes, 166 to thiopyrans, 166

Subject Index

Codimerization, of alkenes, 5 Collman's reagent, 203, 219, 246, 254, 312 Conjugate addition

to enoate esters, 57 to enones, 16, 32, 53-58

Conjugated dienes formation of, 188 1,4-hydrogenation of, 285 reduction of, 287

Cope rearrangement of cyclodecadienes, 161, 131 of cyclodecatrienes, 131 of divinyJcyclobutane, 78

Cross-coupling of alkenyl alanes, 28 of alkenyl boranes, 18 of alkenyl zirconium complexes, 16, 17 of 'TI'-allyl complexes, 27 asymmetric, 13 biaryls from, 49-52 with silyl enol ethers, 14 with vinyl halides, 12-14, 26, 28

Cyanoalkyl ethers, hydrogenation of, 321 Cyclic codimerization, 79, 80, 89 Cyclic cooligomerization

of butadiene and alkenes, 130 of butadiene and alkynes, 116, 131, 135 of butadiene and allene, 131

Cyclization, intramolecular to five-membered rings, 97 to four-membered rings, 84 by nickel-promoted coupling, 136 by reductive coupling, 63, 139 to seven-membered rings, 123 to six-membered rings, 1I8 to three-membered rings, 76

Cycloalkanes, from aromatics, 291 Cycloalkanones, 67 Cycloalkenes

from dicarbonyl compounds, 63, 139 metathesis of, 61

Cyclobutadiene, complexes of, 78 Cyclodesilylation, of butenyl silanes, 76 Cyclodimerization

of alkenes, 82 of allenes, 83 of butadiene, 78, 87, 88,114,124 of 1,2,4-trienes, 116

Cycloheptenones from butadiene, 123 from a,a'-dibromoketones, 120

Subject Index

CycJohexadienes from arenes, 38 by cycJoaddition of alkene and alkyne, 110 by cycJoaddition of alkyne and diene, 116

CycJohexadienyl complexes from 'IT-arene complexes, 36, 37 in cycJohexadiene formation, 38

CycJohexenes from 1,3-dienes, 114 disproportionation of, 20 from 1,2,4-trienes, 116

CycJooligomerization, of butadienes, 68 CycJopentamerization, of allene, 134 CycJopentanones

from 2-acetoxymethyl-3-allyltrimethylsilane, 92

from alkylidenetetrahydrofurans, 104 dehydrogenation of, 375 from a,a'-dibromoketones, 90

CycJopentenones from alkenes, or alkynes, 95 from alkenyl methyl ketones, 103 from J3-allenic bromides, 98 from cycJopentanones, 375 from a,a'-dibromoketones, 91 from 1,3-dienes, 96 from methylenecycJopentanones, 185

CycJopropanation of alkenes, 70 asymmetric, 73 of a,J3-unsaturated derivatives, 70

CycJopropenation of alkynes, 75 of aIkynols, 76

CycJopropyl methyl ketones, 76 Cyc1otetramerization, of alkynes, 127 CycJotrimerization

of alkynes, 85, 105 of allene, 114 of butadiene, 129 catalysts for, 106

Damsin, to isodamsin, 185 cis-Decalin to cis-9-decalol, 344 Decarbonylation, 260--262, 289 Decomplexation

of arenes, 34, 36, 40 ceric ion for, 176 ferric chloride for, 176 Me3NO for, 176

Dehalogenation of aryl halides, 337 of dihalides to alkenes, 62-M

Deoxygenation of epoxides, 58 of ketones and aldehydes, 62-M

435

Diallyl ethers, to unsaturated aldehydes, 181 I ,2-Diaza-1 ,5,9-cycJododecatrienes, 171 Diazoacetates, 70 Diazonium salts

to anhydrides, 243 to ary lalkenes, 48 to carboxylic acids, 204

a,a' -Dibromoketones to bicycJic ketones, 122 to cycJoheptenones, 120 to cycJohexanones, 119 to cycJopentanones, 90 to cycJopentenones, 91

Diels-Alder reaction, 88, 106, II Dienes

to acyl dienes, 256 to cis-alkenes, 285 from alkenyl halides, 28 cyclic co-dimerization of, 79 cyclic co-oligomerization of, 116, 130, 131,

135 cyclodimerization of, 78, 87, 88, 114,

124

cycJooligomerization of, 69 cyclotrimerization of, 129 dimerization of, 23, 24 epoxidation of, 352 hydroesterification of, 222, 223 to oxocycJopentyJcarboxylic acids, 209 telomerization of, 25 trimerization of, 24

gem-Dihalogenoalkanes to alkenes, 62 in Simmons-Smith reaction, 70

Dihydrofurans from aminoalkynes, 159 from J3-diketones and alkenes, 159

Diketones 1,3-, see acetylacetonates from alkynes, 360 1,2-, reduction of, 306

Dimerization of alkenes, 10-12 of cycJoalkenes, 61 of 1, 3-dienes, 23, 24

436

Diols 1,2-, by reductive cyclization of

ketoaldehydes, 10 1 1,1-, stabilization of, 307

Dioxanes, 163 Dithiopyrans, 166 Double-bond migration, 185

Enamines from allylamines, 182 to ketones, 360

Enolate anions addition to cyclohexadienyl complexes, 39 allylic alkylation by, 20-23 in conjugate addition, 56

Enones 'IT-allyl complexes from, 20 conjugate addition to, 32, 53-58

Enynes from alkenyJ halides, 30 conjugated, 29

Epoxides from alkenes, 5, 351 to alkenes, 64, 65

Esters from alkenes, 220-226 J3-alkoxy, from alkenes, 231 to anhydrides, 213, 241-243 from carboalkoxymercuric halides, 225 dienoic,

from alkynes, 230 from dienes, 223 .

from ethers, 213, 214, 372 fonnate-, from alcohols, 212 from halides, 214--220 J3-hydroxy, from epoxides oxalate-, from alcohols, 212

Ethers from acetals or ketals, 300 oxidation to esters, 372

Filtration, under inert atmosphere, 400 Fonnylation, of aryl halides, 247 Furans, from a-bromoketones, 160

Glove bags, 397, 398 Glove boxes, 397 Glycols, 346, 348

Grignard reagents addition to alkenes, 9 ortho-alkylation by, 45

Subject Index

in conjugate addition, 44, 53, 54 cross-coupling with halides, 6, 9, 12-14,

26,42 in ester synthesis, 220 reactions with silyl ethers, 14

1,6-Hexadienes to cyclopentenes, 103 to methylenecyclopentanes, 102

Hydrazones, to phthalimidines, 241 Hydroalumination, of alkynes, 15, 16 Hydrocarboxylation

of alkenes to carboxylic acids, 205-211 of alkynes, 210-212 catalysts for, 205, 206 isomerization during, 206 selectivity in, 206

Hydrocyanation, of butadiene, 4, 174 Hydroesterification

of alkenes to esters, 220-226 of dienes, 222

Hydrofonnylation of alkenes, to aldehydes, 3, 174, 247-252 in presence of functional groups, 251 reversal of, 261 selectivity in, 249, 250

Hydrogen cleavage of, 270, 271 migration of, in alkenes, 177

Hydrogenation asymmetric, 331 catalysts for, 26fr 269 industrial processes, 267 mechanism of, 270 partial

of a1kynes, 274 of aromatics, 295, 297 of dinitro compounds, 318 of heterocycles, 298 of nitro groups, 316 of polyalkynes, 279 of polyenes, 282, 285 of pyridines, 296

reactivity order in of a1kenes and alkynes, 279, 280 of carbonyl compounds, 310 of nitro compounds, 317 of polyenes, 283, 284

Subject Index

Hydrogenation (cont.) selective

of cyanoalkenes, 323 of 1,2-diketones, 288, 290 of nitroalkenes, 314, 316 of nitroalkynes, 274 of polyhalogeno-compounds, 338 of substituted double bonds, 287 of a,~-unsaturated carbonyl compounds,

287,305,308 specific

of alkenes, 280 of alkynes, 276-278 of benzene, 293

see also reduction; transfer-hydrogenation Hydrogenolysis

of acetals and ketals, 300 of aryl halides, 334 of benzyl alcohols, 292, 301, 339 of heterocyclic halides, 335

Hydrosilylation asymmetric, 332 of carbonyl compounds, 304

Hydroxyaldehydes, 307 Hydroxyalkenes, 308 Hydroxylamines, from nitro-compounds, 316 Hydroxyl group, protection of, 180 Hydroxytropolones, 192 Hydrozirconation

of alkenes, 174, 206, 224 of alkynes, 16

Imidazoles from alkenes and ammonia, 169 from amines and CC4, 168

Imidazolines, 168 Imidazolones, 169 Imides, from unsaturated amides, 236 Imines

to amines, 324 from nitriles, 323 to piperidines, 151

Indazolines, 167 Indoles

from N-allyl anilines, 150 from ortho-allyl anilines, 149 from 2-aryl azirines, 148

Indones, by vinylic arylation, 48 Industrial processes, table of, 4 Inert atmosphere techniques, 397-401

437

Iodoarenes, coupling of, 138 Iodonium salts, in aryl ketone synthesis, 255 Isoaromatization, 190 Isocoumarins, from 2-alkenyl benzoic acids,

164 Isocyanates

from azirines, 260 from nitro-compounds, 259-260 to piperidones, 151 to pyridones, 152

Isoindoles, 2-aryl, 145 Isoindolines, 145 Isoindolinones, 146 Isomerization

in alkene dimerization, II of alkenes, 173-193 of allylic alcohols, 47 in hydrocarboxylation, 206 in hydrogenation, 276, 285 in Koch reaction, 200, 207 of steroidal dienes, 176 of vinyl copper intermediate, 18

Isonitriles to imidazolones, 169 to 2-oxazolines, 170 to pyrroles, 147 to pyrrolines, 144

Isoquinolines, I-hydroxy, 153 Isoquinuclidines, 144

Karasch reactions, 9, 53, 54 Ketals

ethers from, 300 formation of, 289

Ketoaldehydes, reduction of, 307 Ketoalkenes, reduction of, 309 Ketoesters, from dibydrofurans, 180 Ketones

from acyl halides, 43 from alkenes, 249, 255-258 to alkenes, 62 from alkyl halides, 254 from aikynes, 257-258 from allylic alcohols, 47, 181 from amines, 366 from aryl alkanes, 358 from aryl Grignard reagents, 254 from aryl iodonium salts, 255 from enamines, 360 to furans, 160

438

Ketones (cont.)

from organomercury compounds, 258, 259 to 2-oxazolines, 170 reduction of,

aliphatic, 300 aromatic, 301 asymmetric, 331 preferential, 307

Keulemans' rule, 250 Koch Synthesis, 199, 200, 206-208

Lactams from aminoalkenes, 143, 236-238 from halogeno-amines, 143, 235

Lactones from alkenes and carboxylic acids, 160 from alkenes and water, 225, 226 from alkynes, 228-232 from a1kynols, 161,227 from anhydrides, 311 to anhydrides, 242 from halogeno-alcohols, 216-219 a-methylene, from homoallylic alcohols,

161 ~ .. y-unsaturated, from epoxyalkenes, 164 from unsaturated alcohols, 223

Lindlar catalyst, 385

McMurry's reagent, 139 Metal carbonyls, 392-393 Metal hydride reductions

catalysts for, 273 of conjugated aldehydes, 308 of ketoaldehydes, 307 of nitroarenes, 314 of a, ~-unsaturated aldehydes, 291 of a,~-unsaturated ketones, 309

Metallacyclopentadienes, 84, 110, 112 Metallacyclopentanes, 97 ortho-Metallation, in synthesis, 44, 238-241 Metathesis

of alkenes, 58-61 cyclic products from, 134

Methylene cycloalkenes, 99, 137 Morpholino-enamines, 91

Naphthalene acetoxylation of, 350 oxidation, to phthalonic acid, 369

Natural products, via carbonylation, 216, 217

Subject Index

Nickel catalysts containing, 388, 389 in coupling reactions, 136 tetracarbonyl, toxicity of, 8

Nitriles hydrogenation of, 320 to pyridines, 154

Nitroalkanes, 25, 26 Nitroalkenes, 25, 26, 318 Nitroalkynes, 274, 317 Nitroarenes, to isocyanates, 259-260 Nitroso-compounds, 324 Nucleophilic substitution

in "IT-arene complexes, 33-39 in aryl halides, 41, 43

Octadienes, 25 Olefins, see Alkenes Oligomerization

of alkenes, 10 of dienes, 23, 24

2-0xazolines, 170 Oxidation, Oximes

from nitro compounds, 316 reduction of, 324

Oxindoles, 146

Palladation, 48 Palladium catalysts, preparation of, 382, 386 1,4-Pentadienyl halides, from allyl halides, 29 Phase transfer catalysis, 201-203, 315 Phenols

from alkynes, 211 to benzo-2-furanones, 162 from cyclohexenones, 191 oxidative cleavage of, 369 telomerization with dienes, 25

Pheromones, via metathesis, 60 Phosphine ligands, chiral, 327 Phosphonium salts, 47 Photocycloaddition, 81 Phthalimidines, 238-240 Pinacolic coupling, 101 Piperidines

from butadiene, 151 from glutaraldehyde, 150

Piperidones from dienes, 151 to pyridinones, 188

Subject Index

Platinum catalysts, preparation of, 386, 387 metals, reactivity and recovery of, 392-397

Polyenes, reduction of, 282, 380 Polymerization

of 1,3-dienes, 23, 24 of cycloalkenes, 61

Polymers, hydrogenation of, 280 Propenylamides, from allylamides, 183 Propenyl ethers, from allyl ethers, 179 Protecting groups

for alkenes in hydrogenation, 382 for amines, allyl as, 182 dimethyl carbinol as, 317 for hydroxyl, 180

Pyrans, from butadiene, 163 Pyridines

from alkynes, 154-156 from nitriles, 6 from 'Y,&-unsaturated ketoximes, 156

Pyridones from alkynes and isocyanates, 152 from 2,4-pentadienamides, 153 from piperidones, 188

Pyrroles, 147, 148 Pyrrolines, 144, 145

Quinazolinones, 168, 169 Quinolines

from N-acryloyl-ortho-bromoanilines, 154 from aromatic amines and aldehydes, 157

Quinolones, from iodoanilines and maleates, 46,47, 153

Rearrangement of alkylidenetetrahydrofurans, 104; see also

Isomerization Reduction, 265-341; see also Hydrogenation Reductive coupling

of dibenzylideneacetone, 100 of 1,3-diols, 77 of diones, 62-64, 139

Rhodium catalysts for asymmetric hydrosilylation, 333 preparation of, 380-382

Rosenmund reduction, 310, 334 Rugulovascines, 186 Ruthenium catalysts, preparation of, 389, 390

Schiff bases, see Imines Schlenk apparatus, 398 SHyl enol ethers, cross-coupling with, 14 Simmons-Smith reaction

in asymmetric cyclopropanation, 73 for cyclopropane formation, 70

Sondheimer reaction, 68, 134 Steroids

carbonyl group reduction in, 303 double-bond reduction in, 288

Substituent effects in alkene metathesis, 61 in 'I1'-arene complexes, 37 in conjugate addition, 57 in 'I1'-cyclohexadienyl complexes in reductive coupling, 64 in Ullmann coupling, 52

Telomerization, of dienes, 25, 26 Terpenoids, 27 Tetrahydro-2-furanones, 160, 163 Tetrahydrofurans, 158 Tetrahydropyranones

from alkynols, 164 from a,j3-unsaturated esters, 163

Thiobenzophenones, to thiolactones, 166 Thiophenes, 166 Transfer hydrogenation

catalysts for, 272 of cyclic ketones, 303 of dinitro compounds, 319 hydrogenolysis via, 336 of nitro groups, 314 of unsaturated aldehydes, 309

Trimerization, of 1,3-dienes, 24

Ullmann coupling reaction, 51, 52 a,j3-Unsaturated compounds

aldehydes, to aldehydoalkanes, 287 from diallyl ethers, 181 to hydroxyalkenes, 308

ketones, cyclic, 183 from dial1yl ethers, 181 to ketoalkanes, 287

Ureas,234

439

Vinyl arenes, from alkenes, 45-48 onho-Vinyl benzamides, cyclization of, 153

440

Vinyl halides cross-coupling of, 12-14, 26--28 to a,J3-unsaturated compounds

amides, 234-235 carboxylic acids, 201 esters, 215-219

Wacker process, 4

Wakamatsu synthesis, 211 Wilkinson's catalyst, 380, 381 Wolff-Kishner reduction, 301

Ynones,32

Ziegler catalysis, 292

Subject Index

Compound Index

Page numbers in italic type refer to compounds mentioned in experimental procedures.

l-Acenaphthaldehyde, 310 l-Acenaphthoyl chloride, 310 Acetaldehyde, 344 Acetamide, 212 Acetic acid, from methanol, 3,4,97, 196,

199,200 Acetic anhydride, 241 Acetonitrile

in alkene metathesis, 58 carbonylation solvent, 204, 205

4-Acetoxy-l-bromo-2-methyl-2-butene, 27 l-(l-Acetoxyethyl)cyclopentene, 23 2-Acetoxymethyl-3-a1lyltrimethylsilane, 92 3-Acetoxymethylenecyclopentane, 97 8-Acetoxy-l,6-octadiene, 25 Acetylacetone

metal complexes from, 390 to pentanediol, 325

3-Acetyl-2,5-dimethyl-I,5-phenyl-4,5-dihydrofuran, 159

Acetylene to acrylic acid, 210 to bifurandione, 162, 229 to cyclopentanone, 258 to cyclopentenone, 258 to dimethyl maleate, 228 to 2,5-hexadienoic acid, 211 to methyl j3-benzoyl propanoate, 230 to methyl 2,5-hexadienoate, 230 to methyl 2,4-pentadienoate, 277 to succinic acid, 210

441

Acetyl iodide from iodomethane, 196, 197, 199,242,244

N-Acetyl norvaline, 212 3-Acetylpyridine, 296 Acetylrehine, 367 3-Acetyl-l,4,5,6-tetrahydropyridine, 296 Acrolein dimethyl acetal, 46, 47 Acrylic acid, 210 Acrylonitrile

acylation of, 254 to j3-cyanopropionaldehyde, 251

a-Acylaminoacrylic acids, 330 Adipaldehyde, 360 Adipic acid

from cyclohexane, 345 from tetrahydrofuran, 214

Adiponitrile, 4, 174 Allene, 83, 131 Allyl acetate

hydrogenolysis of, 351 with norbornene, 81 reduction of, 340

Allyl alcohol butanediol, manufacture of, 251 cyclodimerization of, 158 with norbomadiene, 81 from propargyl alcohol, 278

Allylarnines to enarnines, 182 to 2-pyrollidone, 236

2-Allylaniline, 149

442

Allylbromide addition to I-hexyne, 29 coupling to biallyl, 27 primary amine protection, 182

Allyl chloride to 2,5-hexadienonic acid, 211 to iron allyl complex, 90 to oxocycJopentyl acetic acids, 209

Allylic alcohols, 309 Allyl-l-methylallyl ether, 181 Alnusone dimethyl ether, 50 4-Amino-2-butene, 236 Aminomethylaryl ketones, 331 l-Aminomethyl-3-cycJohexene, 236 4-Amino-2-nitroalkylbenzenes, 318 3-Aminophenylacetylene, 318 2-Aminopyridine, 155, 335 Ammonium chloroplatinate, 396 Androst-5-ene-3,17-diol, 357 Aniline

toN-phenyl benzarrride, 235 to N-phenyl phenylacetarnide, 234

p-Anisoyl propionic acid, 301 (p-Anisyl)butyric acid, 301 Anthracene, 299 Apopinene

from myrtenal' 261, 262, 263 Arenediazonium salts, 204, 205 Aryl amines, 315 Arylmethylenechroman-4-ones, 187 Azirines, 2-aryl, 148 Azobenzene

to 2-phenyl-l-H-indazolone, 238, 239, 241

Benzaldehyde from allylbenzylethers, 180 to 2,6-dibenzylphenol, 192 to I-phenyl-hept-l-ene, 64

Benzaldehyde phenylhydrazone, 240, 241 Benzanthracene, 297 Benzene

carbonylation solvent, 203 chromium complexes, 37 hydrogenation of, 293

Benzimidazole, 169 Benzoacepinone, 157 Benzobutyrolactone, 216, 218, 219 BenzocycJobutenes, 85, 108 Benzo-2-furanone, 162 Benzoic acid

from benzene diazonium salt, 204, 205 from chlorobenzene, 201

Benzoic acid (cont.)

from iodobenzene, 203 from toluene, 344

Benzonitrile

Compound Index

to N-benzylphthalimidine, 240 palladium complex of, 382

Benzothiazole, 169 Benzoxazole, 169 Benzyl acetate, 350 Benzyl amine, 234 Benzyl benzoate, 220 Benzyl bromide, 254 Benzyl chloride

to N-butyl phenylacetate, 216 to N-phenyl phenylacetarnide, 234

Benzylidene chromanone, 187 3-Benzylidene-2-oxindole, 146 Benzylidene tetralone, 191 N-Benzyl-a-methylene-~-lactam, 143 N-Benzyl-N-2-methyl-5-isopropylaniline,

193 N-Benzyl-~-methylpropiolactam, 237 2-Benzylnaphthol, 191 N-Benzylphthalimidine, 240 N-Benzylpyrrole, 147 I-Benzyl-3-pyrroline, 145 N-Benzyl-I,2,3,4-tetrahydroisoquinolin-I-one,

152 Biallyl, 27 Bifurandione, 162, 229 2,2' -Bipyridines, 6, 155 1,3-Bis(diphenylphosphino)butane, 327 1,2-Bis(diphenylphosphino)ethane, 93,

388 2,4-Bis(diphenylphosphino)pentane, 327 1 ,2-Bis(diphenylphosphino )propane, 327 3,3-Bis(iodomethyl)oxetane, 105 Bis(trimethylsilyl)acetylene, 85, 107, 110 trans-8 ,9-Bis(trimethylsilyl-3,4 ,4a,5 ,6, 10b-

hexahydro-2H-naphtho-[ 1 ,2-b )pyran, 110

5,6-Bis(trimethylsilyl)indan, 108 Boron trifluoride, 199 endo-Brevicomin, 165 4-Bromoacetophenone, 50 Bromobenzene

to N-benzyl benzarnide, 234 to N-phenyl benzarnide, 235

o-Bromobenzoic acid, 52 p-Bromobenzoic acid, 201, 202 4-Bromobenzonitrile, 216 2-Bromomethyl benzyl alcohol, 219

Compound Index

I-Bromonaphthalene, 15 5-Bromo-I,4-nonadiene, 29 I-Bromo propene, 12 2-Bromo propene, 113 3-Bromopyridine, 247 ~-Bromostyrene, 234 Butadiene

to alkyl 3-pentenoate ester, 222 cooligomerization of

with allene, 131 with butylisocyanide, 123 with butyne, 131 with cyclic alkynes and diynes, 135 with ethylene, 5, 79, 130 with nitropropane, 26

to dialkyl adipate, 222 to dibenzyl trans-3-hexene-I,6-dioate,

225 cyclooligomerization of, 69

dimerization of, to 1-5-cyclooctadiene, 124 to divinylcyclobutane, 79 to 2-methylene vinylcyclopentane, 87 to 2-methylvinylcyclopentane, 88 to 4-vinylcyclohexene, 114

hydrocyanation of, 4, 174 to isopropyl-3,8-nonadienoate, 223 nickel dodecatrienyl from, 133 telomerization of, 25, 26 trimerization of,

to 1,5,9-cyclododecatriene, 129 to 1,3,6,10-dodecatetraene, 24

R-I,3-Butanediol, 325 1,4-Butanediol, 251 Butanoic acid, 206 I-Butaitol

to N-acetyl norvaline, 212 from propene, 248

I-Butene, ll, 12 2-Butene

from trans-I-bromopropene, 12 from ethylene, 11, 12 from 2-pentene, 59

3-Butenoic anhydride, 243 2-Buten-2-o1, 251, 252 n-Butyl benzoate, 216 n-Butyl-4-cyanobenzoate, 216 t-Butyl-2-(l-cyclopentenyl)hexanoate, 98 t-Butyl-2-cyclopentylidene hexanoate, 98 n-Butyl isocyanide, 123 n-Butyl magnesium bromide, 42 n-Butyl-4-methoxybenzoate, 216

n-Butyl phenylacetate, 216 Butyl phenylamine, 323 Butyne,132 3-Butyn-I-oI, 76 'Y-Butyrolactone

to glutaric anhydride, 242 from succinic anhydride, 311 from tetrahydrofuran, 372 from trimethylene oxide, 214

trans-4-Carbomethoxystilbene, 46 Carbon tetrachloride, 245 N-Carboxynortropidine, 150 ~-Carotene, 63 Carvone, 191, 363 Catechol, 295 Cembrene, 137 Chloroauric acid, 395 Chlorobenzene

to benzoic acid, 201 chromium complex, 35, 36 manganese complex, 35

Chloroborane, 18 I-Chloro-2-butene

to 5-heptanoic acid, 209 to octadienes, 26 to 3-pentenoyl chloride, 244

3-Chloro-I-butene to octadienes, 26 to 3-pentenoyl chloride, 244

4-Chloro-2-buten-I-ol, 219 P-Chloro-~a·p-butenolide, 233 I-Chlorocamphane, 357 4-Chlorocrotonic acid, 347 5-Chloro-l,4-nonadiene, 29 I-Chloronorcamphor, 357 l-Chloro-9-octadecene, 61 Chloroprene, 223 ~4-Cholesten-3,6-dione, 358 Cholest-4-ene, 345 Chromium acetylacetonate, 390 Chromium benzene tricarbonyl, 37, 285,

391

Chromium, chlorobenzene tricarbonyl, 35 Chromium, ethylbenzene tricarbonyl, 40 Chromium hexacarbonyl, 391

complexes of, 33,37

443

Chromium, indan-I-one tricarbonyl, 35 Chromium, tris(l,4-diaza-1 ,3-diene), 24 Chromium, tris(pyridine)tricarbonyl, 33, 34 Chromous sulfate, 277, 281 Chrysanthemate esters, 73

444

( + )-Citronellal, 119 Citronellal-trans-enamine, 182 Cobalt acetate, 203 Cobaltate, tetracarbonyl sodium, carbonylation

catalyst, 202, 203, 214, 231, 234, 256 Cobalt, benzyl tetracarbonyl, 202 Cobalt, camphorquinonedioximes, 74 Cobalt, cyclopentadjenyl dicarbonyl, 85, 107 Cobaltocene, 387 Cobalt octacarbonyl

aIkynol complex, 30, 31 carbonylation catalyst, 202, 203, 205, 211,

213,221,222,229,236,238,240, 241,242,253,255,258

epoxide deoxygenation, 65 hydrogenation catalyst, 299 properties of, 392, 393

Cobalt pentacyano anion hydrogenation catalyst, 286 hydrogenation mechanism, 271

Cobalt polysulfide, 274, 317 Cobalt tetracarbonyl hydride

carbonylation catalyst, 205, 206, 212, 223 in hydrofonnylation, 248, 249 isomerization catalyst, 251

Cobalt trisacetylacetonate, 95 Cobalt, tris(trimethylphosphite)allyl, 293 Coniferyl alcohol, 159 Conjugated dienes, partial reduction of, 286 Copper(I) chloride

amines to fonnamides, 233 grignards to enones, 54

Copper(ll) chloride carbonylation of alkenes, 224, 225 carbonylation of vinyl complexes, 233

Copper(i) iodide, 57 Copper methyl, 54 Copper(I) oxide, 207 Copper triftate, 82 Copper, m-triftuoromethylphenyl, 50 Crotonamide, 237 4-Cumyloxycyclopentenone, 32 (::!: )a-Cuparenone, 92 Cuprate, bis(a-trimethylsilylvinyi)lithium, 56 Cuprate, dimethyl lithium

cyclization of enones, 56 with tetrahydroftuorenone, 54

Cuprate, di(a-methyoxyvinyl)lithium, 56, 57 Cuprate, diphenyl lithium

addition to enones, 44 phenylation, 43, 52

Cuprate, di-n-propyllithium, 18

Compound Index

Cuprates, dialkyllithium, 99 Curvularin, 216, 217 ~-Cyanopropionaldehyde, 251 2-(2-Cyanopropyl)lithium, 35, 37 Cyclobutanones, 185 Cyclodecadiene, 130, 275 Cyclodecane, 281 (E)-Cyclodecen-2-one, 375 Cyclodecenyne, 275 Cyclododecene, 281 1,5,9-Cyclododecatriene, 6, 68, 129 Cycloheptenones, 120, 122 1,9-Cyclohexadecadiene, 61 Cyclohexane, 293, 344 Cyclohexanol,305, 344 Cyclohexanone

from cyclohexane, 344 to 2,6-dibenzylphenol, 192 from phenol, 295 reduction of, 305, 307

Cyclohexano-2-pyrollidone, 236 Cyclohexene

from dibromocyclohexane, 62 to methylcyclopentanecarboxylic acid, 207 photocyclization of, 82 in transfer hydrogenation, 319

Cyclohexenone with lithium cuprates, 56 reduction of, 290

Cyclohexylmagnesium bromide, 12 Cyclooctadiene

1,3- , 175, 176 1,5- , 175, 176 from butadiene, 68, 126

Cyclooctadienol, 353 Cyclooctatetraene, 127 Cyclooctene, 61 Cyclopentadienide sodium, 387 Cyclopentane, 98 Cyclopentanoic acid, 209 Cyclopentanones, 93 Cyclopentenes, 103, 186 Cyclopentenone, 186 Cyclopropenes, 76 Cyclopropyl methyl ketone, 359 Cyclotetradecene, 63

Damsin, 185 cis-Decalin, 344 cis-9-Decalol, 344 2,4,6,8-Decatetraene-I,4:7,IO-diolide, 162 I-Decene, 64

Compound Index

4,4'-Diacetyl biphenyl, 50 Diallyl ether, 243 Diarninopyridine, 335 Diaza-I,5,9-cyclodecatriene, 171 Diazomethane, 72 Dibenzyl-trans-3-hexene-l,6-diolate, 225 Dibenzylidenacetone, H)() 3,7-Dibenzylidene-l, 2-cycloheptanedione, 192 2,7-Dibenzylidene cycloheptanone, 192 2,6-Dibenzylidene cyclohexanone, 192 2,6-Dibenzylphenol, 192 p-Dibromobenzene, 201 1,4-Dibromobutane, 98 vic-Dibromocyclohexane, 62 a,a' -Dibromoketones

to cycloheptenones, 120 to cyclohexanones, 119 to cyclopentanones, 90 to cyclopentenones, 91

Dibromomethane,98 2,4-Dibromopentan-2-one, 92 1,3-Di-n-butylbenzene, 42 1,3-Dichlorobenzene,42 3,4-Dichlorobenzoyl chloride, 261 1,l-Dichloromethylethylene, 138 2,4-Dichloropyrimidine, 335 1,9-Dichloro-2,5,8-trimethylenenonane, 138 Dicyclohexylethylamine, 231 2,3-Diethyl-5-carboethoxy-2,4-pentadiene-4-

lactone, 231 Diethylketone, 255 N,N-Diethylnerylamine, 182 9,lO-Dihydroanthracene, 299 5,6-Dihydrobenzanthracene, 297 Dihydrojasmone, 181 2,5-Dihydro-4-methylfurfuryl alcohol, 158 5,6-Dihydro-4H-l,3-oxazine,170 Dihydropyran, hydroformylation of, 251 4,5-Dihydropyrene, 299 2,3-Dihydro-2-vinylbenzofuran, 158 1,4-Dihydroxybut-2-ene, 147 Diiodochloromethane, 70 Biiodomethane, 70 1,3-Diiodopropane, 105 Diisobutyl aluminium hydride

in conjugate addition, 32 in cross coupling, 49

DiisopropyJidene succinic anhydride, 243 3,5-Dimethoxy benzyl chloride, 217 2,5"Dimethoxy-2,5-dihydrofurans, 180 3,6-DimethoxY-2-nitroaniline, 320 5,5-dimethyl-3-acetylcyclohexanone, 57

Dimethylacetylene dicarboxylate, 84 a,a-Dimethylallyl benzyl ethers, 180 2-Dimethylarninomethylbiphenyl, 50 3-N,N-Dimethylarninoprop-l-ene,276 3-N,N-Dimethylarninoprop-I-yne, 276 cis-3,3-Dimethylazetidinone, 144 N,N-Dimethylbenzylamine

to N-methylphtl\i!ijmidine, 239 phenylation of, Sl'}

445

2,2-DimethylbutanOiI acid, 200 2,2-Dimethyl-3-buten-I-ol, 223 3-trans-4,4-Dimethylbuten-I-ylcyclohexanone,

16 3,3-Dimethylbutyne, 16 trans-3-(3,3-Dimethyl-I-butynyl)-4-

cumyloxycyclopentanone, 32 4,5-Dimethyl-c,c,t-I,4,7-cyclodecatriene, 131,

132 1,2-Dimethyl-I,4-cyclohexadiene, 118 N,N-Dimethylcyclohexylarnine, 367 3,3-Dimethylcyclopropene, 113 3,3-Dimethyl-I,4-diphenyl-2-azetidinone, 143 Dimethyldiphenylmaleate, 228 Dimethylformamide, 201 2,5-Dimethyl-3-hexyn-2,5-diol, 243 1,3-Dimethylindole, 150 Dimethylmaleate

from acetylene, 228 alkylation of, 21 to quinolones, 46, 47

5,5-Dimethyl-3-(a-methoxyvinyl)cyclohexanone, 57

Dimethyl neohexynylaluminium, 32 E-2,7-Dimethylocta-2,4,6-triene, 24 2,7-Dimethyl-2,4,6-octatriene, 24 2,2-Dimethylpentanoic acid, 206 2,4-Dimethyl-pentan-2-0I, 344 2,5-Dimethyl-3-phenylcyclopent-2-enone, 92 5,9-Dimethyl-2-pheny Isulfonyldeca-(E)-4, 8-

diene,23 2,2-Dimethylpropanoic acid, 200 Dimethyl sulfoxide, 201

Dimethyl exo-tricyclo[4.2.I.Olnon-3-ene-3,4_ dicarboxylate, 84

2,4-Dinitroalkylbenzenes, 318 DIOP: see 2,3-IsopropyJidene-2,3-dihydroxy-

I ,4-bis( diphenylphosphino )butane Diphenylacetylene, 228 Diphenylcrotonolactone, 228 1,2-Diphenyl-I,4-cyclohexadiene, 118 1,2-Diphenylcyclopropane, 77 Diphenylcyclopropenone, 94

446

1,I-Diphenylethylene, 83 1,8-Diphenylnaphthalene, 52 1 ,3-Diphenyl-l ,3-propanediol, 77 Divinylcyclobutane, from butadiene, 68, 78,

79 Dodecane, 285 2-Dodecanone. 359 1,3,6,1O-Dodecatetraene,24 Dodecene

carboxylic acids from, 206 to dodecane, 285

I-DOPA, 3, 326

l-Epoxydecene, 64 Ergosta-l,2,2-dien-3-one, 288 Ergosta-l,4,2,2-trien-3-one, 288 d,I-Estrone, 110 Ethene: see Ethylene Ethyl acrylate, 254 Ethyl benzene, 5, 40 Ethyl bromoacetate, 231 Ethyl-5-bromovalerate, 255 2-Ethylbutanoic acid, 206 Ethyl-2-butynoate, 18 Ethyl diazoacetate, 72 Ethyl trans-2,3-di-n-propylcyclopropene-l

carboxylate, 72 Ethylene

by I-alkene metathesis, 60 dimerization of, II, 12 to 5-heptanoic acid, 209 hydroformylation of, 250, 255 to ~-propiolactone, 226 to 4,4,4-trichlorobutanoyl chloride, 245

Ethylene glycol, 182 2-Ethyl hexanol, 248 Ethyl-6-ketooctanoate, 255 2-Ethyl-3-methyl-quinoline, 157 Ethyl-3-(5,6,7,8)-tetrahydroisoquinoline, 156 Ethyne see Acetylene 2-Ethynylcyclohexanol, 227 2-exo-Ethynyl-7 -syn-norbomanol, 227 Eugenol, 189, 190

Famesyl acetate, 27 Ferrate (1-), benzoyl tetracarbonyl, 254 Ferrate (1-), dicarbonyl cyclopentadienyl, 65 Ferrate (1-), hydrido tetracarbonyl, 246 Ferrate (2-), tetracarbonyl, 98, 203, 219, 246,

254, 312 Ferrocene, 2, 387

Compound Index

Ferrocene, I-diphenylphosphino-I'-dimethylaminomethyl, 13, 14

Formaldehyde, 381, 385 Formylpropionic acid, 312 Furfural, 371 Furoic acid, 371

Geraniol, 353 Geranyl acetate

allylic alkylation of, 23 by allylic coupling, 27

Glutaric anhydride, 242 Glutarimide, 237 Gradisol, 79

Hepta-l,5-diyne, 279 Hepta-l,6-diyne, 108 Heptanal, 360 Heptanoyl bromide, 262 I-Heptene, 222 3-(and 5-)Heptenoic acid, 209 2-Heptylcyclohex-5-enone, 187 2-Heptylcyclohex-2-enone, 187 10,12-Hexadecadien-I-ol, 279 I-Hexadecene

to 15-triacontene, 60 to 9-tricosene, 60

trans-Hexa-l,4-diene, 5 cis-Hexa-I,4-diene, 352 Hexa-I,5-diene, 97 Hexa-2,5-dienoic acid

from acetylene, 211 to phenol, 211

Hexa-I,5-dien-3-ol, 354 Hexa-2,5-dienoylbromide, 244 Hexa-I,5-diyne, 85

dl-Hexahydromandelic acid, 292 exo-Hexahydro-4,7-methanoinden-l-one, 258 Hexahydro-3-methylene-4, 7-

methanocyclopenta(b )pyran-2(3H)-one, 227

Hexamethyl phosphoric triamide, 19 Hexanal

to I-phenyl-hept-I-ene, 64 protection of, 307

Hexanoic acid, 206 Hexan-loOI, 200 I-Hexene, 249 3-Hexene, 59 trans-Hex-I-enyl diisobutylalane, 15 trans-Hex-I-enylnaphthalene, 15

Compound Index

I~Hexyne, 29 3-Hexyne, 231 Hirsutene, 184 Homoisoftavone, 187 Humulene, 137 Hydrazine

in catalyst preparation, 384 as hydrogen-transfer reagent, 319 reaction with imines, 323

Hydridocarbonyltris( triphenylphosphine) rhodium(l), 381

Hydrogen cyanide, 4, 174 Hydrogen iodide, 199, 242 Hydroquinone, 295 4-Hydroxy-2-butanone, 325 4-Hydroxycyclohexanone, 295 3-( I-Hydroxyethyl)piperidine, 297 I-Hydroxy-3-phenylisoquinoline, 153

Imidazolone, 166, 169 3-Imino-2-phenylindazoline, 167 l-Indanone, 35 Indazolone, 166 2-Iodoaniline, 46, 47 4-Iodoanisole, 216 Iodobenzene

to n-butyl benzoate, 216 to methyl ~-benzoyl propionate, 230

4-Iodobenzoic acid, 7 2-Iodobenzyl alcohol, 216, 218, 219 l-Iodo-3-chloropropane, 14 4-Iodocyclohexanol, 15 2-Iodo-3,5-dimethoxybenzyl(phenyl)sulfide,

217 E-3-Iodo-3-hexene, 215 Iodomethane

to acetyl iodide, 196-199, 242, 244

alkylation of ethylbenzene by, 39-41 to hydroxybutenolides, 231, 232

4-Iodonitrobenzene, 49 l-Iodo-8-phenylnaphthalene, 52 Iridic acid, hexachloro, 303 Iridium chloride, 395 Iridium, chlorocarbonyl

bis(triphenylphosphine), 389 Iridium, dichlorohydride

tris( dimethylsulphoxide), 272 Iridium, trihydrido tris(triphenylphosphine),

302 Iron, bis(cyclooctadiene), 118 Iron(llI) chloride, 64

447

Iron, dicarbonylcyclopentadienyl, cation propene complex, in ~-lactam synthesis,

237 protecting group, for double bonds, 282

Iron, dicarbonylcyclopentadienyl, dimer, 90, 245

Iron, dodecacarbonyl, tri, 315, 392, 393 Iron(II) iodide, 65 Iron, nonacarbonyl, di, 90, 120, 392, 393 Iron, pentacarbonyl

in carbonylation reactions, 204, 210, 220, 246, 254, 257

properties of, 392 reaction with dibromoketones, 91, 120 reduction of nitroarenes by, 315 toxicity of, 8

Iron, tricarbonylcyclobutadienyl, 78 Iron(llI), tris(dibenzoylmethido), 12 Isobutyronitrile, 35, 37 Isodamsin, 185 trans-Isoeugenol, 189, 190 Isoindole, 145 Isoindoline, 145 Isoprene

cooligomerization of, 132 cyclodimerization of, 125 dimerization of, 24 epoxidation of, 353 1,2-hydrogenation of,

to l-isopropenyl-2-methyl-2-vinylcyclobutane, 79

to 4-methyl-3-pentanoate esters, 223 Isopropenyl acetate, 31 2,3-Isopropylidene-2,3-dihydroxy-l,4-

bis( diphenylphosphino )butane (DIOP), 327

Isopropyl 3,8-nonadienoate, 223 lsoquinoline, 298

7-Ketocholesteryl benzoate, 357

~-Lactam-N-benzyl-a-methylene, 143 Limonene, 284 Lithium aluminium hydride

anhydride reduction, 312 with copper iodide, 290 with titanium tetrachloride, 62--65

Lithium dialkyl cuprates, 99 Lithium diisopropylamide, 37

Magnesium oxide, 230 Mandelic acid, 292

448

Manganese decacarbonyl, 234 Manganese, pentacarbonyltrimethylsilyl, 253 p-Menth-l-ene, 353 Menthol

to menthone, 362 from menthyl a1lylether, 180

Menthone, 362 Menthyl a1lylether, 180 Menthyl diphenylphosphine, 328 Mesitylene, 38 Metal carbonyls, 392, 393 Methanol

to acetic acid, 4, 196, 199, 200 in hydroesterification, 220

3-endo-Methoxycarbonyl-5-exo-methoxynortricyclene, 225, 226

4-Methoxy-2,5-dinitroanisole, 320 5-Methoxy-l-naphthol, 369 Methoxynorpregnatetraene, 21 4-(4-Methoxyphenyl)-4-(2-

dimethylaminoethyl)-2-cyclohexen-lone, 39

3-Methoxyphthalic acid, 369 6-MethoxytetraIone, 345 a-Methoxyvinyl lithium, 57 Methyl acetate, 242 Methyl acrylate, 10 N-Methylacylamide, 238 4-(2-Methylallyl)cyclohexanol, 15 2-Methylallyl ethers, 180 N-Methylaziridine, 142 3-Methylbutanal, 250 Methyl butanoate, 221 2-Methyl-I-3-butenenitrile, 174 2-Methylbut-3-yn-2-ol, 127 2-Methylcarbopenam, 238 Methyl ciruiamate, 225 Methyl copper, 18 I-Methylcyclobutene, 359 Methylcyclohexane, 208 5-Methyl-2-cyclohexen-I-one, 44 I-Methylcyclopentanecarboxylic acid, 207 Methyldiazoacetate, 76 Methyldibromoacetate, 70 5-Methyl-4,5-diphenyl-2-oxazoline, 170 2-Methylenecyclohepta-5-enone, 123 Methylenecyclopentanes, 103 Methylenecyclopropane, 80, 93 5-Methylene-I,3-dioxanes, 180 4-Methylenetetrahydrofurfuryl alcohol, 158 3-Methylene tricyclo[4.2.1.0]non-3-ene, 81

Compound Index

2-Methylenevinylcyclopentane from butadiene, 68, 87 from methylenecyclopropane, 93 from 2,7-octadienylisopropyl ether, 104

2-Methyl-2-ethylbutanoic acid, 200 cis-Methyl-2,5-hexadienoate, 230 2-Methylhex-4-enal, 181 Methyl-3-hydroxybutyrate, 214 Methyl-3-hydroxypropionate, 214 I-Methylindan-l-ol, 35 3-Methylindole, 150 2-Methylindole, 149 Methyl-4-iodobenzoate, 46 Methylisobutyrate, 221 3-Methylisocoumarin, 165 2-Methyl-5-isopropylphenol, 191 Methyl lithium, 35 Methyl magnesium bromide, 54 3-Methyl-3-methoxycarbonyl-5-phenyl-l-

pyrroline, 145 Methyl-4-methylene-I,2,3,4-

tetrahydroquinoline, 152 Methyl-3-methylhexanoate, 222 9-Methyl-9-nitro-I,6-decadiene, 26 2-Methyl-4-(3-nitrophenyl)-3-butyn-2-ol,

317 Methyl octanoate, 222 Methyl-2,4-pentadienoate, 227 2-Methyl pentanoic acid, 206 2-Methyl-l-pentene, 222 3-Methyl-l-pentyn-3-ol, 76 Methyl phenylacetate, 39, 40, 41 3-Methyl-5-phenylcyclohexanone, 44 3-Methyl-4-phenylcyclopentenone, 104 Methylphenylisobutyrate, 39, 40, 41 methylphenylsulfonyl acetate, 23 N-Methyl phthalimidine, 239 2-Methyl propanoic acid, 206 2-Methyl propene, 250 Methyl propiolate, 127 2-Methyl pyridine, 37, 391 3-Methyl-2-pyrollidone, 236 Methyl sorbate, 115 3-Methylsuccinimide, 237 N-Methylsuccinimide, 238 p-Methylsulfonylbenzaldehyde, 356 Methyl-3 ,3 ,4,4-tetracyanocyclopentane

carboxylate, 90 2-Methylvinylcyclopentane, 88 2-Methyl-3-vinyloctanal, 181 Modhephene, 186

Compound Index

Molybdenum cyclopentadienyltricarbonyl dimer, 245

Molybdenum dichlorodinitrosylbis-(triphenylphosphine), 59

Molybdenum hexacarbonyl, 72 a-Morpholino styrene, 92 cis,cis-Muconic acid, 369 Myrtenai, 261, 262, 263

I-Naphthaldehyde, 262 p-Naphthylacetic acid, 203 a-Naphthylmagnesium bromide, 13 a-Naphthyltriftuoroacetate, 350 Nickel acetate, 301 Nickel acetylacetonate

in acetylene cyclotetramerization, 127 in conjugate addition, 32 cross-coupling catalyst, 14 isomerization catalyst, 189, 390

Nickel, ('IT-allyl)bromo, dimer with acetylene, 244 with allyl bromide, 27

Nickel, bis(1,5-cyclooctadiene) cooligomerization of,

butadiene + aikenes, 130 butadiene + aikynes, 117, 131, 135 butadiene + allene, 131 butadiene + butylisocyanide, 123 strained aikenes, 80

cross-coupling catalyst, 50 oligomerization of,

allene, 124, 134 butadiene, 78, 114, 124, 129 dimethylcyclopropene, 83 methylenecyclopropane, 94

preparation of, 389 Nickel, bis(N-methylsalicylaidimino), 31 Nickel, bromo(1, l-dimethyl-'lT-allyl), dimer,27 Nickel chloride, 230 Nickel, dicarbonylbis(triphenylphosphine)

alkyne trimerization, 106 allene trimerization, 114 cooligomerization catalyst, 114

Nickel, dichloro-l,2-bis( diphenylphosphino )ethane

cross-coupling catalyst, 13, 42 preparation of, 388

Nickel, dichlorobis(phosphine), 388 Nickel, dichlorobis(triphenylphosphine)

cross-coupling catalyst, 14 preparation of, 388

Nickel, dichloro(-DIOP) cross-coupling catalyst, 13 preparation of, 388

449

Nickel, dihalobis(triaikylphosphine) butadiene dirnerization, 87 methylenecyclopropane dimerization, 94

Nickel dodecatrienyl, 133 Nickel,'lT-2-methylailylbromide, dimer, 15 Nickel,a,w-octadiendiyl, 123 Nickel tetracarbonyl

'IT-ailyl complexes from, 14 in carbonylation, 195, 201, 204, 205, 210,

211, 213, 215, 230, 234, 259 coupling allylic halides, 136 I ,2-cyclic enediones formation, 94 geranyl acetate synthesis, 27

Nickel tetrakis(tri-isopropylphosphite), 80 Nickel, tetrakis(triphenylphosphine)

cross-coupling catalyst, 31, 50 cyanation catalyst, 42

Nitric oxide, 213 p-Nitroaniline, 320 4-Nitrobiphenyl, 49 4-Nitrobromobenzene, 51 Nitrocyclohexane, 316 3-Nitrophenylacetylene, 318 2-Nitropropane, 7, 26 p-Nitrotoluene, 350 Nonadecane-5,15-dione, 139 3,8-Nonadienoic acid, 223 5-Nonane, 301 Norbomadiene

with aikenes, 80 with allene, 84 carbonylation of, 225, 226 to cyclopentanone derivative, 257 to cyclopentenone derivative, 258

Norbomene with aikenes, 80 allylation of, 81 with dimethylacetylenedicarboxylate, 84

9-Octadecene, 60 2,6-Octadiene, 26 Octadienes, 25 Octadienylphenylether, 25 n-Octanol, 25 1,3,7-Octatriene, 24 irans-4-Octene, 72 3-n-Octyl-'Y-butyrolactone, 160 2-Octyn-l-ol, 31

450

Osmate(2-) ,hexachloro , 100 Osmium tetroxide, 395, 396 Oxalic acid, 213 Oxocyclopentyl acetic acid, 209 3-0xo-l,4-steroids, 288

Palladium acetate alkene arylation catalyst, 46 with alkenyl boranes, 18 carbonylation catalyst, 204, 205, 215, 216,

223, 235, 243 cross-coupling catalyst, 28, 29 cyclization of 1,6-hexadienes by, 103 with diazomethane, 72 recovery from palladium residues, 384,

395 Palladium, acetato('IT-allyl), dirner, 24 Palladium, bis[ 1,2-

bis(diphenylphosphino)ethane], 22 Palladium,

bis(triphenylphosphine )benzoquinone, 88

Palladium black, 49 Palladium,

bromo(phenyl)bis(triphenylphosphine), 235

Palladium, carbonyl bis(triphenylphosphine), 247

Palladium(D) chloride 'IT-allyl complexes from, 20, 21 carbonylation catalyst, 222, 225, 226--228,

233, 243, 259 onho-rnetallation by, 238

Palladium, chloro ('IT-allyl) dimer, 20 Palladium, chloro-

(butanoyl)bis( triphenylphosphine), 221 Palladium,

chloro(hydrido )bis( triphenylphosphine), 221

Palladium, chloro ('IT-methoxynonpregnatetraene), dimer, 21

Palladium, diacetato bis(triphenylphosphine), 43,46

Palladium, dibromo bis(triphenylphosphine), 247

Palladium, dichloro bis(benzonitrile) 'IT-allyl complexes from, 19 carbonylation catalyst, 201 cross-coupling catalyst, 29 cyclization catalyst, 102 preparation of, 382

Compound Index

Palladium, dichloro bis(triphenylphosphine) carbonylation catalyst, 201, 205, 216, 221,

222, 234, 247 cross-coupJing catalyst, 49 preparation of, 383 telomerization catalyst, 26

Palladium, dichloro(cyclooctadiene), 225, 226 Palladium, dichloro(norbomadiene), 225, 226 Palladium,

iodo(phenyl)bis(triphenylphosphine), 49 Palladium, maleic anhydride

bis(triphenylphosphine), 24, 83, 88 Palladium, on basium sulphate

for acid chloride hydrogenation, 310 for alkyne partial hydrogenation, 275 decarbonylation catalyst, 262, 263 hydrogenolysis catalyst, 334

Palladium, on charcoal hydrogenation catalyst for,

alkynes, 274 aromatics, 295, 297 carbonyl groups, 301 nitro groups, 313, 316

isoaromatization catalyst, 190 transfer hydrogenation catalyst for,

acid chlorides, 311 dinitro compounds, 319

transfer hydrogenolysis catalyst, 334--338 preparation of, 385

Palladium, tetrakis(triphenylphosphine) alkyne arylation catalyst, 43 allylic alkylation catalyst, 22, 23 cross-coupling catalyst, 26, 31, 42 cyanation catalyst, 42 preparation of, 383

Palladium triftuoroacetate, 19 Pentanediol, 325 2,4-Pentanedione: see Acetylacetone 1-Pentanol, 200 1,2,4-Pentatriene, 116 I-Pentene, 206 2-Pentene, 59, 106 Pentenenitrile, 174 3-Pentenoylchloride, 244 Pentenyloxyhexadiyne, 110 I-Pentyn-3-o1, 76 4-Pentyn-l-ol, 227 Phenethylarnine, 322 Phenol

from acetylene and allyl chloride, 211 to cyclohexanone, 295 telomerization with butadiene, 25

Compound Index

Phenylacetic acid, 203 Phenylacetonitrile, 322 Phenylacetylene, 231 N-(~-phenylacryloyl)pyrollidine, 234 N-Phenyl benzaldimine, 239 N-Phenyl benzanride, 235 2-Phenyl butadiene, 126 I-Phenylcyclooctadiene, 126 3-Phenyl-2,4-dioxo-I,2,3,4-

tetrahydroquinazoline, 166 I-Phenylethyl magnesium chloride, 13 I-Phenyl hept-I-ene, 64 Phenylhydroxylamine, 316 2-Phenyl-I-H-indazolone, 238-241 Phenyl isobutyronitrile, 35, 37 2-Phenyl isoindolinone, 146 3-Phenyl isoindolinone, 147 Phenyl lithium

with coordinated chlorobenzene, 35 with coordinated mesitylene, 38 to lithium diphenylcuprate, 44 to 4-nitrobiphenyl, 49 onho-phenylation by, 50

Phenyl magnesium bromide, 220 Phenyl mesitylene, 38, 49 N-Phenylphthalimidine, 240, 241 a-(and ~-)phenyl propanal, 252 a-phenyl propiolactone, 219 2-Phenylpyridine, 6, 155 Phenyl vinyl ether, 82 Phenyl zinc chloride, 49 Phosphoric acid, 199 Phthalaldehydic acid, 312 Phthalic anhydride, 312 Phthalide, 216, 218, 219 Phthalirnide, 183 Phthalonic acid, 369 2-Picoline, 391 a-Pinene. 349 Pinocarveol, 349 Piperidine, 295 2-Piperidone, 151, 236, 297 Platinic acid, hexachloro

carbonylation catalyst, 205, 206, 221 to Pt02 (Adams' catalyst), 387 preparation of, 395, 396

Platinum, dichloro bis(benzonitrile), 250 Platinum, dichloro bis(triphenylarsine), 221 Platinum, dichloro bis(triphenylphosphine),

313, 333 Platinum, dichloro bis(triphenylphosphite), 221 Platinum on carbon, 274, 297

Platinum(lV) oxide (Adams' catalyst) for hydrogenation of,

aikynes, 274 aromatics, 291, 297 carbonyl groups, 300 nitro groups, 313 preparation of, 387

451

Platinum, tetrakis(triphenylphosphine), 386 Platinum/tin catalyst, 271, 283, 290 Platinum, tris(triphenylphosphine), 386 Propargyl acetate, 134 Propargyl alcohol

alkylation of, 30 cyclopropanation of, 76 reduction of, 278 tetramerization of, 127

Propene: see Propylene Propenylamide, 183 Propenylcyclohexane, 12 Prophos: see 1,2-

Bis( diphenylphosphino )propane ~-Propiolactone

from ethylene, 226 to succinic anhydride, 242

PropionaJdehyde. 182, 183 Propylene

carbonylation to acids, 206 carbonylation to esters, 220, 221 hydroformylation of, 248

Propylene oxide, 214, 352 Prostaglandins, 186 Pyrene, 299 Pyridine, 58, 154, 156, 294 3-Pyridine carboxaldehyde, 247 2-Pyridone, 153 Pyrimidine, 335 Pyrrole, 147 Pyrrolidine, 234 2-Pyrollidone, 236 1-Pyrroline, 144

Quadricyclane, 95 Quinoline, 46, 47, 154, 298, 310

Raney copper, 318 Raney nickel

asymmetric hydrogenation, 325 nitrile hydrogenation, 320 nitro group hydrogenation, 313 nitroso, oxime and imine hydrogenation,

324 Resorcinol, 295

452

Retinal, 63 Rhodium, carbonylhydridotris

(triphenylphosphine), 249, 250, 252 preparation of hydrofonnylation catalyst,

381 Rhodium carboxylate

cyclopropanation catalyst, 73 cyclopropenation catalyst, 75

Rhodium, chlorobis(ethylene), dimer allene cyclooligomerization by, 134 preparation of, 381

Rhodium, chlorobis(hexa-l ,5-diene), dimer, 331

Rhodium, chlorocarbonyl bis( triphenylphosphine)

decarbonylation catalyst, 61 preparation of, 380 to RhCl(PPh3h, 261

Rhodium, chlorodicarbonyl, dimer carbonylation catalyst, 259 with NEt3, hydrogenation catalyst, 308 preparation of, 382

Rhodium, chlorotris(triphenylphosphine) with citronellal, 119 cyclization of 1,6-hexadienes, 102 decarbonylation of acyl halides, 260 decarbonylation of aldehydes, 260,

289 hydrogenation catalyst,

alkenes, 280 cyanoalkenes, 323 mechanism, 270 nitroalkenes, 318 specific cis-deuteration, 280 steroids, 288 table, 269 a,~-unsaturated ketones, 288, 308

hydrosilylation, 304 ketal formation, 289 metallocycle fonnation, 112 preparation of, 380 transfer hydrogenation catalyst, 272

Rhodium, diene( diphosphine )cation asymmetric hydrogenation, 326 hydrogenation of ketones, 302

Rhodium, diiodo dicarbonyl anion, 196, 197

Rhodium on alumina, 321 Rhodium on carbon

aromatic hydrogenation, 291 nitrile hydrogenation, 323

Compound Index

Rhodium trichloride allylether isomerization, 179 with benzylidenechromanone, 187 carbonylation catalyst, 210 with cyclohexenones, 191 with 1, 3-cyc1ooctadiene, 175 double bond isomerization, 184-186 eugenol isomerization, 190 from rhodium metal, 395 methyl acrylate dimerization, 10 transfer hydrogenation catalyst, 314

Rhodium, tris(tri-isopropylphosphine )hydride imine hydrogenation, 324 nitrile hydrogenation, 322

Rugulovasines, 186 Ruthenium, bis(hexamethylbenzene), 293 Ruthenium, dichlorodicarbonylbis-

(triphenylphosphine), 302 Ruthenium, dichloro tris(triphenylphosphine)

hydrogenation catalyst alkenes, 283 anhydrides, 311 nitro groups, 314, 320 nitroso groups, 324 oximes, 324 steroids, 288 table, 269

preparation of, 389 transfer hydrogenation catalyst, 272

Ruthenium dioxide, 292 Ruthenium, dodecacarbonyl tri-, 233 Ruthenium, hexamethylbenzenechlorohydrido-

triphenylphosphine, 294 Ruthenium on carbon, 317, 319 Ruthenium tetroxide, 396 Ruthenium trichloride, 314

Sebacil, 366 Silver nitrate, 395 Sodium acetate, 204, 205 Sodium amide, 196 Sodium borohydride

with cerium trichloride hexahydrate, 307, 309

with cobalt chloride, 284 with copper acetylacetonate, 314 nickel acetate, 291 nickel tris(triphenylphosphine), 338 palladium chloride, 291 palladium tetrakis(triphenylphosphine), 340 rhodium trichlorotrispyridine, 294

Compound Index

Sodium hydride, 203 Sodium hydroxide, 201 Sodium neopentoxide, 203 Sodium perruthenate, 395 Stannous chloride: see Tin(II) chloride Steroidal-3-alcohols, 303 Stilbene, 64 Styrene

hydroformylation of, 252 to methyl cinnamate, 225

2-Styrylindole, 148 Succinic acid

from acetylene, 210 from succinic anhydride, 311

Succinic anhydride, 311 Sulfuric acid

carbonylation catalyst, 199 in Koch synthesis, 200, 207

R,R-Tartaric acid, 325 Terephthalic acid, from p-Xylene, 5, 344, 368 Testosterone, 366 Tetrabutylammonium iodide, 201 1,2,4,6-Tetracarbomethoxycycloocatetraene,

127 Tetracyanoethylene, 89 Tetracyclin, 346 Tetrahydroftuorenone, 54 Tetrahydrofuran, 214 Tetrahydro-2-furanone, 163 Tetrahydrofurfuryl alcohol, 158 Tetrahydropyran-2-carboxaldehyde, 251 Tetrahydropyranone, 163 3,4,5,6-Tetrahydropyridine, 297 3,3,5,5-Tetramethylcyclohexanone, 54 1,2,3,4-Tetramethyl-5-vinyl-I,3-

cyclohexadiene, 118 3,4,5,5-Tetraphenylcyclopent-3-ene-I,2-dione,

94 Tetraphenylethylene, 62 3-Thiophenecarboxylic acid, 372 Thiourea

with NiCb, carbonylation catalyst, 230 with PdCb, carbonylation catalyst, 227, 228

Tin(II) chloride carbonylation co-catalyst, 205, 206, 221,

222,250 hydrogenation co-catalyst, 300

Titanium dicyclopentadienyl dichloride, 276 Titanium tetrachloride, 62-65 Titanocene, 188

Toluene, derivatives of, 339 endo-Trevicomin, 165 1,5-Triacontene, 60 Tri-n-butylarnine, 46 1,3,4-Trichlorobenzene, 261 4,4,4-Trichlorobutanoyl chloride, 245 9-Tricosene, 60 Tricyclo[6.4.0.0]dodecane, 82 trans, trans-Trideca-5,8-diene-7-one, 259 Triethylammonium formate, 336 2.4,5-Triethylimidazole, 169 Triftuoroacetic acid, 38 m-Triftuoromethylphenyl copper, 51 Trimethyl aluminium, 17 1.4,7 -Trimethylenecyclononane, 138 Trimethylene oxide

to 'Y-butyrolactone, 214 decomplexation, 176

Trimethylphosphite, 306 4-Trimethylsilylbutene, 76 4-Trimethylsilyl-5-

453

methoxymethylbenzocyclobutene, 86 2-Trimethylsilyloxy-4-phenyl-I,5-hexadiene,

104 Trimethylsilylpropargyl methyl ether, 86 2,4,5-Triphenylimidazoline, 168 Tris(2-biphenylyl)phosphite, 78, 114, 117,

124, 126, 131, 135 Tris(2,6-dimethyl

phenylimino)diphenylcyclopentene, 96 Tri-o-tolylphosphine

in alkene arylation, 46, 47 in allylic alkylation, 21

Tropolone, 192 'Y-Tropolone derivatives, 123 Tungsten hexachloride, 58-60 Tungsten trichlorophenyl, 59

Undecanal, 360 5-Undecyn-2-one, 31 'Y,8-Unsaturated aldehydes, 181

Valeronitrile, 323 Vanadyl acetylacetonate, 390 Verbenyl acetate, 349 Vinyl acetate, 344, 350 Vinyl bromide, 13 Vinyl chloride, 12, 13 Vinyl cyclobutane, 79 5-Vinylcyclohexa-l,3-diene, 117 4-Vinylcyclohexene, 68, 114

454

Vinyl ioclide, 113 a-Vinyl naphthalene, 13 trans-2-Vinyl-5-phenyltetrahydrofuran, 158 a-VinylpropioIactone, 219

Wilkinson's catalyst: see Rhoclium chlorotris (triphenylphosphine)

p-Xylene oxidation of, 5 in phase transfer catalysis, 202

Zearalenone, 216, 217 Zinc chloride, 17,30,

49

Compound Index

Zirconium chlorodicyclopentadienyl-3,3-dimethylbutenyl, 16

Zirconium chlorohydridodicyclopentadienyl alkenes to carboxylic acids, 206 alkenes to esters, 224 hydrozirconation of alkynes, 16, 17,

28 Zirconium dichlorodicyclopentadienyl, 17

References - Springer978-1-4613-2651-9/1 · References for Chapter 2 405 42. T. Mitsuyasu and J....

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