Volume II

COMPOUNDS OF GERMANIUM, TIN AND LEAD

INCLUDING BIOLOGICAL ACTIVITY AND COMMERCIAL APPLICATION

ORGANOMETALLIC COMPOUNDS

METHODS OF SYNTHESIS

PHYSICAL CONSTANTS AND CHEMICAL REACTIONS

Edited by

MICHAEL DUB

Central Research Department, Monsanto Company

Volume II

COMPOUNDS OF GERMANIUM, TIN AND LEAD

INCLUDING BIOLOGICAL ACTIVITY AND COMMERCIAL APPUCA TION

Second Edition, Edited by

RICHARD W. WEISS

Organic Division, Monsanto Company

Covering the Literature from 1937 to 1964

Springer Science + Business Media, LLC 1967

ORGANOMETALLIC COMPOUNDS Second Edition

VoI. 1 - Compounds of Transition Metals, published in 1966

VoI. IlI-Compounds of Arsenic, Antimony, and Bismurh, in preparation

ISBN 978-3-642-51891-1 ISBN 978-3-642-51889-8 (eBook) DOI 10.1007/978-3-642-51889-8

AII rights reserved, especially thar of teanslatiao into foreigo languages

It is also forbidden tO reproduce this book, e'ther whole or in part, by phoromechanical meanS

(photostat, microfilm andlor microcard Ot any other means)

wirhout written permission from the Publisbers

© 1967 by Springer Scienee+Business Media New York Originally published by Springer-Verlag New York, Ine. in 1967

Library of Congress Catalog Card Number 66-28249

Tirle No. 4358

PREFACE TO THE SECOND EDITION

The aim of this compilation has been to provide a comprehensive, non­critical source of information concerning organometallic compounds. The scope is limi~ed to the compounds containing at least one carbon-metal bond. The information includes methods of preparation, properties, chemical reactions, and applications.

The First Edition comprised the literature from 1937 to 1958. The Second Edition is completely revised and extended through 1964. The literature prior to 1937 was thoroughly covered by E. Krause and A. von Grosse in ''Die Chemie der metall-organischen Verbindungen," Verlag von Gebrueder Borntraeger, Berlin, 1937.

Our work consists of three volumes. Volume I contains derivatives of the transition metals of Groups III through VIII of the Periodic Table. Volume II contains derivatives of germanium, tin, and lead. Volume III contains derivatives of arsenic, antimony, and bismuth.

The compilation is based on searches through Chemical Abstracts. The collection of references for 1964 was completed before the Subject Indexes to Volumes 60 and 61 of the Abstracts were available; thus some omissions in the coverage of that year are possible.

We have attempted to make the .. coverage of the literature complete in order that the compilation may have best ~i1ity to the chemist, chemical engineer, patent attorney, and editor. In the interest of brevity, certain numerical data are omitted, but references to the original literature are given. Yield data are rounded to two significant figures. Wherever possible, tables have been used. The entries in the Bibliography section include references to Chemical Abstracts.

I am indebted to Dr. R. S. Gordon, Director of the Central Research Department, and to Mr. W. A. Wilkinson, Head of the Information Center, Monsanto Company, for their generous support of this project. I am also indebted to Dr. R. W. Weiss, the Coeditor of Volume 11, for his invaluable advice on the form of this compilation. My thanks are due to the library staff at the Information Center for their assistance and especially to Mrs. Mary Alice Doiron for the preparation of the typescript for the photo-offset printing.

St. Louis, Missouri January 1966

V

Michael Dub

INTRODUCTION TO VOLUME II

Volume II of the series ''Organometallic Compounds" covers organic deriva­tives of germanium, tin, and lead. The term organometallic compound is used in the strictest sense and includes only compounds with at least one metal­carbon bond. We attempt to present complete information on the organic derivatives of the three metals. Literature.data for each compound are given in separate paragraphs on SyntheSis, Properties, Chemical Reactions, and Addition Compounds. Two new entries not covered in Volume I for Use and Biological Properties are added. This recognizes the commercial interest reflected in numerous publications connected with the industrial application of organometallic derivatives of tin and lead.

To facilitate the use of this volume and to allow correlation of analogous organometallic derivatives of germanium, tin, and lead, the individual com­pounds are listed systematically. A decimal system is used to characterize chapters and subchapters. Similar compounds of each metal can be found under corresponding numbers. The system and arrangement will be obvious from the Table of Contents. The main chapters are as follows:

1. Symmetric tetraorganometal compounds - R4M 2. Unsymmetric tetraorganometal compounds - RnMR'4-n 3. Organometal hydrides - Rn~-n 4. Organometal compounds containing heteroatom-metal bonds - RnMX4-n 5. Organo-polymetal compounds, e.g. ReSQ2 6. Bimetallic compounds, e.g. R3PbLi 7. Cyclic organometal compounds, e.g. CH2(CH2)3Ge~ 8. Polymerization reactions and unspecified compounds 9. Commercial application.

The arrangement within the main chapters follows three simple principles: order with decreaSing number of metal-carbon bonds; order with increaSing complexity of organic groups; consistent use of a sequence of heteroatoms.

The compounds are listed in order of the organic moieties linked to the central metal in the series aliphatic, aromatic, heterocyclic, unsaturated, and functionally substituted groups; aralkyl groups are arranged according to the location of the carbon-metal bond within the above series. The following examples illustrate location of certain groups: benzyl follows methyl but precedes ethyl; tolyl follows phenyl and precedes naphthyl; and 2-indenyl or 9-fluorenyl follows cyclopentadienyl.

The sequence of the heteroatoms as substituents follows the reverse of their position in the Periodic Table, i.e., halogen, oxygen and homologues, nitrogen and homologues, etc. A group of closely related substituents, with often uncertain linking atoms, is listed as pseudohalides and follows halo­gen. This group comprises (iso)cyanide, (iso)cyanate, (iso)thiocyanate, azide, and cyano complexes. All salts or esters of oxygen acids, excluding

VII

carboxylic acids, are combined under Salts. Polyfunctional groups are listed under the heteroatom next to the central metal or under the function first appearing in the system. Cross references are given. The nomencla­ture is generally in agreement with Chemical Abstracts.

For helpful discussions and criticisms my thanks are due to my colleagues Drs. M. W. Dietrich, B. Dmuchovsky, and Q. E. Thompson. I am indebted to Mary Alice Doiron for the preparation of the typescript and her skill in arranging the tables. I am glad to acknowledge the contributions of Erika Weiss in collecting and checking references, technical assistance, and reading the proof.

Monsanto Company Organic Division St. Louis, November 1966

R. Weiss

VIII

ABBREVIATIONS

The following abbreviations are used in addition to, or at variance with, those in Chemical Abstracts:

cat. corr. dec. DMF

Fc GLC IR liq. m. M

mat!. obtd. prod. psi PVC Py ref. r. t.

rxn. sub!. substd. THF TLC

UV

catalyst corresponding decomposition, d~composes, decomposed, decomposing dimethylformamide ferrocenyl radical, CsHsFeCs14-gas-liquid chromatography infrared liquid (adjective) melting point, melts at, melted at a metal atom in generic formulae material(s) obtained product{s) pound per square inch pressure polyvinyl chloride pyridine re ference( s) room temperature reaction( s) sublimes at, sublimed at, sublimation substituted tetrahydrofuran thin-layer chromatography ultraviolet

IX

CONTENTS

PREFACE TO THE SECOND EDITION III

INTRODUCTION TO VOLUME II V

ABBREVIATIONS VII

GERMANIUM

2. 2.1 2.4 2.4.1

2.5

2.5.1

2.6 2.6.1 2.6.2 2.6.3 2.6.3.1 2.6.3.3 2.6.3.4 2.6.4 2.6.5 2.7 2.7.1 2.7.2 2.7.3 2.7.6 2.7.7

3. 3.1

3.2 3.3 3.6 3.8

SymmetriC Tetraorganogermanes 1

Unsymmetric Tetraorganogermanes Nonfunctional Derivatives 4 Unsymmetric Tetraorganogermanes with Olefinic Substituents 13 Unsymmetric Tetraorganogermanes Containing Functionally

Substituted Olefinic Groups 19 Unsymmetric Tetraorganogermanes with Acetylenic Sub-

stituents 19 Unsymmetric Tetraorganogermanes Containing Functionally

Substituted Acetylenes 24 Functionally Substituted Unsymmetric Tetraorganogermanes 27 Tetraorganogermanes Containing Halogen 27 Tetraorganogermanes Containing Pseudohalogen Substituents 28 Tetraorganogermanes Co~taining Oxygen 32 Organogermanes with Hydroxy Groups and Their Derivatives 32 Tetraorganogermanes Containing Carbonyl Groups 36 Tetraorganogermanes Containing Carboxyl Functions 38 Tetraorganogermanes Containing Sulfur 42 Tetraorganogermanes Containing Nitrogen and Phosphorous 42 Tetraorganogermanes Containing Metal Substituents 45 Bridged Bisorganogermanes 45 Tetraorganogermanes Containing Organosilyl Substituents 48 Tetraorganogermanes Containing Organotin Substituents 48 Tetraorganogermanes Containing Group II Metals 51 Tetraorganogermanes Containing Alkali Metals 52

Organogermanium Hydrides Nonfunctional Organogermanium Hydrides Unsymmetric Organogermanium Hydrides Deuterium-Substituted Organogermanium Hydrides Functionally Substituted Organogermanium Hydrides Organogermanium Hydrides Containing Heteroatom-

Germanium Bonds Mixed Organogermanium Hydride Halides Organogermanium Hydrides Containing Other Germanium­

Heteroatom Bonds

XI

52 58 59 59

4.

4.1 4.1.1 4.1.1.1 4.1.1.2 4.1. 1.6 4.1.2 4.1.2.1 4.1.2.6 4.1.3 4.1.3.1 4.1.3.4 4.1.3.6 4.2 4.2.1 4.2.4 4.3 4.3.1 4.3.1.1 4.3.1.2 4.3.1.3 4.3.2 4.3.3 4.3.5 4.3.5.1

4.3.5·6

4.4 4.4.1 4.4.2 4.4.7 4.5

5. 5.1 5·2

5.3

6. 6.1 6.5

Organogermanium Compounds Containing Heteroatom-Germanium Bonds

Compounds with Halogen Triorganogermanium Halides Unsubstituted Symmetric Triorganogermanium Halides Unsymmetric Unsubstituted Triorganogermanium Halides Functionally Substituted Triorganogermanium Halides Diorganogermanium Dihalides Unsubstituted Diorganogermanium Dihalides Functionally Substituted Diorganogermanium Dihalides Organogermanium Trihalides Unsubstituted Organogermanium Trihalides Unsaturated Organogermanium Trihalides Functionally Substituted Organogermanium Trihalides Organogermanium Salts Organogermanium Pseudohalides Organogermanium Salts or Esters of Oxygen Acids Organogermanes with Germanium Oxygen-Bonds Organogermanium Oxides and Hydroxides Triorganogermanium Oxides and Hydroxides Diorganogermanium Oxides Monoorganogermanium Oxides and Germanoic Acids Organogermanium Peroxy Compounds Organogermanium Alkoxides and Mixed Oxides Organogermanium Carboxylates Organogermanium Carboxylates with Unsubstituted

Carboxylic Acids Organogermanium Carboxylates Derived from Functionally

Substituted Carboxylic Acids Organogermanium Compounds with Sulfur and Selenium Organogermanium Sulfides, Disulfides, and Selenides Organogermanium Mercaptides and Mercaptans Metal-Substituted Organogermanium Sulfides and Selenides Organogermanium Compounds with Nitrogen, Phosphorous,

Arsenic, Antimony, and Bismuth Organogermanium Amides, Imides, Nitrides, and Phosphides Organogermanium Metal Imides Organogermanium Imido Phosphoranes and Arsenic or

Antimony Analogues

Organo-polygermanes Hexaorganodigermanes Organo-polygermanes Containing More Than Two Germanium

Atoms Organo-polygermanes Containing Heteroatoms

Bimetallic Organogermanes Organogermanes Containing Germanium-Metal Bonds Bimetallic Organogermanium Derivatives with Metal

Coordination Compounds

XII

65 65 65 70 70 77 77 79 83 83 85 89 93 93 93 99 99 99

102 102 104 106 112

112

112

119 119 121 123

125 125 125

125

128 129

130 132

133

138

7.4.1 7.4.3

7·5

8.1

TIN

1. 1.1 1.3 1.4 1.6

1.6.1 1.6.2

2. 2.1 2.3 2.4 2.4.1

2.6

2.6.1 2.6.2 2.6.3 2.6.3.1 2.6.3.2 2.6.3.3 2.6.3.4 2.6.4 2.6.5.1 2.6.5.2 2.7

Cyclic Organogermanes Cyclic Tetraorganogermanes Cyclic Organogermanium Hydrides Cyclic Organogermanium Compounds Containing Heteroatom-

Germanium Bonds Cyclic Organogermanium Halides Cyclic Organogermanes with Germanium-Oxygen Bonds Cyclic Organo-polygermanes

Polymerization Reactions with Organogermanes

Symmetric Tetraorganotin Compounds Nonfunctional Symmetric Tetraorganotin Compounds Symmetric Tetraheterocyclic Tin Compounds Symmetric Unsaturated Tetraorganotin Compounds Symmetric Functionally Substituted Tetraorganotin

Compounds Symmetric Halogen-Substituted Tetraorganotin Compounds Other Symmetric Functionally Substituted Tetraorgano­

tin Compounds

Unsymmetric Tetraorganotin Compounds Unsymmetric Nonfunctional Tetraorganotin Compounds Heterocyclic Substituted Tetraorganotin Compounds Tetraorganotin Compounds with Olefinic Substituents Tetraorganotin Derivatives of Functionally Substituted

Ole fins Tetraorganotin Compounds with Acetylenic Substituents Functionally Substituted Tetraorganotin Derivatives of

Acetylenes Functionally Substituted Unsymmetric Tetraorganotin

142 l~

150 150 153 155

155

172 172

172

176 177 190 193

198 210

211

Compounds 217 Tetraorganotin Compounds Containing Halogen 217 Tetraorganotin Compounds Containing Pseudohalogen Groups 218 Unsymmetric Tetraorganotin Compounds Containing Oxygen 225 Compounds Derived from a Hydroxy Group 225 Peroxy Tetraorganotln Compounds 229 Organotin Compounds Containing Carbonyl Groups 229 Tetraorganotin Compounds Containing Carboxyl Groups 233 Tetraorganotin Compounds Containing Sulfur 238 Tetraorganotin Compounds Containing Nitrogen 240 Tetraorganotin Compounds Containing Phosphorous 240 Tetraorganotin Compounds Containing Organometallic

Substituents 244 Bridged Organotin Compounds 244 Tetraorganotin Compounds with Organosilyl Substituents 2~

Tetraorganotin Compounds with Organogermanium Substituents 2~

XIII

2.7.4 2.7.5 2.7.6 2.7.7 2.8

3. 3.1

3.3 3.5 3.6

4. 4.1 4.1.1 4.1.1.1 4.1.1.2

4.1.1.3 4.1.1.4 4.1.1.6 4.1.1.6.1 4.1.1.6.2

4.1.1.6.3 4.1.1.6.5 4.1.1.6.7 4.1.2 4.1.2.1 4.1.2.3 4.1.2.4 4.1.2.6 4.1.2.6.1 4.1.2.6.2

4.1.2.6.3 4.1.2.6.9 4.1.3 4.1.3.1 4.1.3.3 4.1.3.4 4.1.3.6 4.1.3.6.1 4.1.3.6.9 4.1.4 4.1.4.1

4.1.4.3 4.1.4.5

4.1.5 4.2

4.2.1 4.2.4

Tetraorganotin Compounds with Organolead Substituents Tetraorganotin Compounds with Boron and Aluminum Tetraorganotin Compounds with Group II Metals Tetraorganotin Compounds with Group I Metals Tetraorganotin Compounds with Tin-Carbon Double Bonds

Organotin Hydrides

Nonfunctional Organotin Hydrides Organotin Deuterides Functionally Substituted Organotin Hydrides Organotin Hydrides Containing Heteroatom-Tin Bonds

Organotin Compounds Containing Heteroatom-Tin Bonds

248 252 252 254 254

254

255 265 265 265

Organot in Hal ides 268 Triorganotin Halides 268 Symmetric Unsubstituted Triorganotin Halides 268 Unsymmetric Unsubstituted Triorganotin Halides 286 Heterocyclic Substituted Triorganotin Halides 290 Unsaturated Triorganotin Halides 290 Functionally Substituted Triorganotin Halides 290 Halogen-Substituted Triorganotin Halides 290 Pseudohalogen-Substituted Triorganotin Halides 290 Oxygen-Containing Triorganotin Halides 290 Nitrogen-Substituted Triorganotin Halides 290 Metal-Substituted Triorganotin Halides 290 Diorganotin Dihalides 302 Unsubstituted Diorganotin Dihalides 302

Heterocyclic Substituted-Diorganotin Diha1ides 315 Unsaturated Diorganotin Dihalides 321 Functionally Substituted Diorganotin Dihalides 322 Halogen-Substituted Diorganotin Dihalides 322 Pseudohalogen-Substituted Diorganotin Dihalides 322 Oxygen-Substituted Diorganotin Dihalides 322 Diorganotin Dihalides Containing Nitrogen or Silicon 322 Organotin Trihalides 327 Unsubstituted Organotin Trihalides 328 Heterocyclic Organotin Trihalides 333 Unsaturated Organotin Trihalides 333 Functionally Substituted Organotin Triha1ides 333 Halogen-Substituted Organotin Trihalides 333 Organotin Trihalides with Substituents Other Than Halogen 333 Organotin Halides Containing Tin-Oxygen Bonds 336 Organotin Halides Containing Oxy- or Hydroxy-Groups 337 Organotin Halides Containing Alkoxy Groups 337 Organotin Halides Containing Carboxylate Groups 342

Organotin Halides Containing Tin-Sulfur Bonds 342 Organotin Salts 344 Organotin Pseudohalides 344

Organotin Salts or Esters of Oxygen Acids 347

XIV

4.; 4.;.1 4.;.1.1 4.;.1.2 4.;.1.2.1

4.;.1.2.6

4.;.1.; 4.;.2 4.;.; 4.;.;.1 4.;.;.1.;

4.;.;.1.6.1

4.;.;.1.6.;

4.;.;.1.6.7

4.;.;.1.9 4.;.;.2 4.;.;.2.1 4.;.;.2.;

4.;.;.2.6.1

4.;.;.2.6.;

4.;.;.2.9 4.;.;.2.9.1 4.;.;.2.9.2 4.;.;.; 4.;.4 4.;.5 4.3.5.1

Organotin Oxygen Compounds Organotin Oxides and Hydroxides Triorganotin Oxides and Hydroxides Diorganotin Oxides and Hydroxides Nonfunctionally Substituted Diorganotin Oxides and

Hydroxides Functionally Substituted Diorganotin Oxides and

Hydroxides Monoorganotin Oxides and Hydroxides Organotin Peroxy Compounds Organotin Alkoxides Triorganotin Alkoxides and Phenoxides Triorganotin Alkoxides Derived from Heterocyclic

Alcohols Triorganotin Alkoxides Derived from Unsaturated

Alcohols Triorganotin Alkoxides Derived from Functionally

Substituted Alcohols Triorganotin Alkoxides Derived from Halogen-Sub­

stituted Phenols Triorganotin Alkoxides Derived from Alcohols or

Phenols Containing Oxygen Functions Triorganotin Alkoxides Derived from Alcohols or

Phenols Containing Nitrogen Triorganotin Alkoxides Derived from Organometallic

Substituted Alcohols or Phenols Triorganotin Mixed Oxides Diorganotin Alkoxides Unsubstituted Diorganotin Alkoxides and Phenoxides Diorganotin Alkoxides Derived from Heterocyclic

Alcohols Diorganotin Alkoxides Derived from Functionally Sub­

stituted Alcohols and Phenols Diorganotin Alkoxides Derived from Halogen-Substi­

tuted Phenols Diorganotin Alkoxides Derived from Alcohols or Phenols

;71 ;75 ;78 ;81 ;81

;8;

;8;

;8;

;92 ;92 ;95 ;95

400

400

400

Containing Oxygen Functions 400 Diorganotin Alkoxides Derived from Alcohols or Phenols

Containing Nitrogen 400 Diorganotin Alkoxides Derived from Dihydric Alcohols

or Phenols Miscellaneous Diorganotin Alkoxides Diorganotin Siloxanes Diorganotin Alkoxide Carboxylates Monoorganotin Trialkoxides Organotin Derivatives of Acetals Organotin Carboxylates Triorganotin Carboxylates

xv

400 400 400 400 408 408 408 408

4.3.5.1.1 4.3.5.1.3

4.3.5.1.6.8.1 4.3.5.1.6.8.2

4.3.5.1.9.1 4.3.5.1.9.2

4.3.5.1.9.3 4.3.5.2 4.3.5.2.1 4.3.5.2.3

4.3.5.2.6 4.3.5.2.6.1 4.3.5.2.6.3

4.3.5.2.6.8 4.3.5.2.9 4.3.5.3 4.4 4.4.1 4.4.1.1 4.4.1.2 4.4.1.3 4.4.2 4.4.2.1 4.4.2.1.1

4.4.2.1.3 4.4.2.1.6

Unsubstituted Triorganotin Carboxy1ates Unsubstituted Triorganotin Carboxy1ates Derived

from Heterocyclic Acids Unsubstituted Triorganotin Carboxy1ates Derived

from Unsaturated Acids Unsubstituted Triorganotin Carboxy1ates Derived

from Functionally Substituted Acids Unsubstituted Triorganotin Carboxy1ates Derived

from Halogen-Substituted Acids Unsubstituted Triorganotin Carboxy1ates Derived

from Oxygen- and Sulfur-Containing Acids Unsubstituted Triorganotin Carboxy1ates Derived

from Acids Containing Nitrogen Unsubstituted Triorganotin Carboxy1ates Derived

from Acids Containing Mercury Unsubstituted Triorganotin Carboxy1ates Derived

from Po1yfunc~iona1 Acids Bis-Triorganotin Derivatives of Dicarboxy1ic Acids Unsubstituted Triorganotin Carboxy1ates Derived

from Po1yfunctiona1 Acids Unsymmetric or Functionally Substituted Triorgano­

tin Carboxylates Unsymmetric Triorganotin Carboxy1ates Unsymmetric Triorganotin Carboxy1ates Derived

from Functionally Substituted Acids Functionally Substituted Triorganotin Carboxylates Diorganotin Carboxylates Unsubstituted Diorganotin Carboxy1ates Diorganotin Derivatives of Heterocyclic and

Unsaturated Carboxylic Acids Functionally Substituted Diorganotin Carboxy1ates Halogen-Substituted Diorganotin Carboxylates Diorganotin Carboxy1ates Derived from Acids Substi-

410

417

420

420

420

420

420

426 426

426

426 426

426 426 433 433

439 442 442

tuted with Oxygen, Sulfur, Nitrogen, and Phosphorous 442 Diorganotin Carboxylates of Dicarboxy1ic Acids 442 Diorganotin Carboxy1ates Containing Tin-Sulfur Bonds 446 Monoorganotin Carboxylates 448 Organotin Compounds with Sulfur, Selenium, and Organotin Sulfides, Se1enides, and Tellurides

Tellurium 451 451

Triorganotin Sulfides, Selenides, and Tellurides Diorganotin Sulfides, Selenides, and Tellurides Monoorganotin Sulfides and Selenides Organotin Mercaptides and Organoselenides Triorganotin Mercaptides Unsubstituted Triorganotin Mercaptides and Organo-

selenides Heterocyclic Substituted Triorganotin Mercaptides Functionally Suhstituted Triorganotin Mercaptides

XVI

451 453 456 456 456

4.4.2.2 4.4.2.2.1 4.4.2.2.3 4.4.2.2.6 4.4.2.3 4.4.4 4.4.7

4.5.1 4.5.2 4.5.3 4.5.4 4.5.5 4.5.6

5.3 5.4

6. 6.1 6.4 6.5

7. 7.1 7.3 7.5

8. 8.1 8.2

9.

LEAD

1. 1.1

1.3 1.4 1.6

Diorganotin Dimercaptides 462 Unsubstituted Diorganotin Dimercaptides 462 Heterocyclic Substituted Diorganotin Dimercaptides 464 Functionally Substituted Diorganotin Dimercaptides 465 Monoorganotin Trimercaptides 468 Organotin Thiocarboxylates, Xanthates, and Thiocarbamates 470 Metal-Substituted Organotin Sulfides, Selenides, and

Tellurides Organotin Compounds with Nitrogen, Phosphorous, Arsenic,

Antimony, and Bismuth Unsubstituted Organotin Amides, Imides, and Nitrides Heterocyclic Organotin Imides Organotin Derivatives of Acid Amides and Acid Imides Organotin Metal Imides Organotin Imido Phosphoranes and Imido Stibanes Organotin Phosphides, Arsenides, Antimonides, and

Bismuthides

Organo-Polytin Compounds Hexaorganoditin Compounds Organo-Polytin Compounds Containing More Than Two Tin

Atoms Organo-Polytin Halides Organo-Polytin Carboxylates

Bimetallic Organotin Compounds Organotin Derivatives of Groups II-IV Elements Organotin Alkali Metal Compounds Organotin Derivatives with Transition Metal Coordina­

tion Compounds

Cyclic Organotin Compounds Cyclic Tetraorganotin Compounds Cyclic Organotin Compounds with Heteroatom-Tin Bonds Cyclic Organo-Polytin Compounds

Miscellaneous Organotin Compounds Polymerization Reactions with Organotin Compounds Unspecified Organotin Compounds

Commercial Application of Organotin Compounds

Symmetric Tetraorganolead Compounds Unsubstituted Tetraorganolead Compounds

Symmetric Tetraheterocyclic Lead Compounds Symmetric Unsaturated Tetraorganolead Compounds Functionally Substituted Symmetric Tetraorganolead

Compounds

XVII

470

474 474 476 477 477 477

482

489 492 493

494 496

499

504 508 508

509 515

515

519 529 530

530

2. 2.1 2.3 2.4 2.5 2.6 2.6.1 2.6.3 2.6.4 2.6.5 2.7 2.7.1 2.7.2

3.

4. 4.1 4.1.1 4.1.1.1 4.1.1.3 4.1.1.4 4.1.1.6 4.1.2 4.1.2.1 4.~.2.2

4.1.3 4.2 4.2.1 4.2.4 4.3 4.3.1 4.3.2 4.3.3 4.3.3.9 4.3.5 4.3.5.1 4.3.5.1.1

4.3.5.1.6.1

Unsymmetric Tetraorganolead Compounds Nonfunctional Tetraorganolead Compounds Heterocyclic Substituted Tetraorganolead Compounds Tetraorganolead Compounds with Olefinic Substituents Tetraorganolead Compounds with Acetylenic Substituents Functionally Substituted Tetraorganolead Compounds Tetraorganolead Compounds Containing Halogen Tetraorganolead Compounds Containing Oxygen Tetraorganolead Compounds Containing Sulfur Tetraorganolead Compounds Containing Nitrogen Metal-Substituted Tetraorganolead Compounds Bridged Tetraorganolead Compounds Tetraorganolead Compounds with Metallic Substituents

Organolead Hydrides

Organolead Compounds Containing Heteroatom-Lead Bonds Organolead Halides Triorganolead Halides Unsubstituted Triorganolead Halides Heterocyclic Triorganolead Halides Unsaturated Triorganolead Halides Functionally Substituted Triorganolead Halides Diorganolead Dihalides Unsubstituted Diorganolead Dihalides Substituted Diorganolead Dihalides Monoorganolead Halides Organolead Salts Organolead Pseudohalides Organolead Salts or Esters of Oxygen Acids Organolead Oxygen Compounds Organolead Oxides ~nd Hydroxides Organolead Peroxides Organolead Alkoxides Organolead Siloxanes Organolead Carboxylates Triorganolead Carboxylates Triorganolead Carboxylates Derived

Acids Triorganolead Carboxylates Derived

Acids Triorganolead Carboxylates Derived

Acids Triorganolead Carboxylates Derived

Substituted Acids Triorganolead Carboxylates Derived

Containing Acids Triorganolead Carboxylates Derived

Nitrogen-Substituted Acids

XVIII

from Unsubstituted

from Heterocyclic

from Unsaturated

from Functionally

from Halogen-

from Oxygen- and

532 536 536 536 541 541 541 541 541 547 547 550

550

551 551 552 557 557 557 558 559 561 562 562 562 563 566 566 570 571 571 572 572

573

573

573

573

573

573

4.3.5.2 4.3.5.2.1

4.3.5.3 4.4 4.5

5· 5·1 5.2

6. 6.1 6.5

7.

8. 8.1 8.2

BIBLIOGRAPHY

Diorganolead Carboxylates Diorganolead Carboxylates Derived from Unsubstituted

Acids Diorganolead Dicarboxylates Derived from Substituted

578

579

Acids 581 Monoorganolead Tricarboxylates 582 Organolead Compounds with Sulfur, Selenium, and Tellurium 584 Organolead Compounds with Nitrogen and Phosphorous 586

Organo-Polylead Compounds Hexaorganodilead Compounds 587 Organolead Compounds with Less Than Three Organic

Groups per Lead Atom

Bimetallic Organolead Compounds Organolead Derivatives of Groups I-IV Metals Organolead Derivatives with Transition Metal Coordina-

tion Compounds

Cyclic Organolead Compounds

Miscellaneous Organolead Compounds Polymerization Reactions with Organolead Compounds Unspecified Organolead Compounds

590

591

593

596

596 598

599

REVIEW PUBLICATIONS AND MONOGRAPHS 691

XIX