Synthesis and Physicochemical Investigation of
1
Synthesis and Physicochemical Investigation of Hydrofluorocarbons with Extended -Stacked Arene Units Markus Etzkorn, Department of Chemistry, UNC Charlotte, 9201 University City Blvd., Charlotte, NC 28223 Dienedione 3 is in principle an ideal framework to obtain scaffolds of type 6 by benzannulation and subsequent “coupling” of these intermediates. Since 3 is thermally labile the alcohol intermediates 7 and 8 are potential Whereas diol 8 is prone to trans-annular reactions, hydroxyketone 7 provided a suitable Diels-Alder adduct 10 for functionalization: Dess-Martin oxidation yielded the formal DA- adduct 12 of the parent ( 3 ) which is thermally stable. Cycloaddition with TCTD (9) furnished the bis-adduct 14. Both DA adducts were converted with DDQ under O O O O O O R n R n R n R n R n R n (R = H ,F) 3 4 6 ( 8) O ( 7) OH OH OH NaBH 4 O O ( 3) LiAlH 4 O 7 OH SO 2 Cl 4 9 (TC TD ) O OH Cl Cl Cl Cl 10 O Cl Cl Cl Cl O D ess- M artin reagent CH 2 Cl 2 RT O Cl Cl Cl Cl O O Cl Cl Cl Cl O Cl Cl Cl Cl O Cl Cl Cl Cl O Cl Cl Cl Cl toluene, rflx 13 14 15 DDQ CH 2 Cl 2 DDQ CH 2 Cl 2 9 (TC TD ) 12 ORTEP plot of compound 12 intermediates towar targets of type 6; have obtained crystal structures of derivatives 3 , 7 and 8 . Iso-Indenone Derivatives
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Synthesis and Physicochemical Investigation of Hydrofluorocarbons with Extended p -Stacked Arene Units. Markus Etzkorn, Department of Chemistry, UNC Charlotte, 9201 University City Blvd., Charlotte, NC 28223. - PowerPoint PPT Presentation
Transcript of Synthesis and Physicochemical Investigation of
Synthesis and Physicochemical Investigation of
Hydrofluorocarbons with Extended -Stacked Arene Units
Markus Etzkorn, Department of Chemistry, UNC Charlotte, 9201 University City Blvd., Charlotte, NC 28223
Dienedione 3 is in principle an ideal framework to obtain scaffolds of type 6 by benzannulation and subsequent“coupling” of these intermediates. Since 3 is thermally labile the alcohol intermediates 7 and 8 are potential
Whereas diol 8 is prone to trans-annular reactions, hydroxyketone 7 provided a suitable Diels-Alder adduct 10 for functionalization: Dess-Martin oxidation yielded the formal DA-adduct 12 of the parent (3) which is thermally stable. Cycloaddition with TCTD (9) furnished the bis-adduct 14. Both DA adducts were converted with DDQ under mild conditions to their corresponding chlorinated arene derivatives 13 and 15.
O
O
O
OO
ORn
Rn
Rn
Rn
Rn
Rn
(R = H, F)3 4 6
(8)O (7)
OH
OH
OHNaBH4
O
O (3)
LiAlH4
O
7
OH SO2
Cl4
9 (TCTD)O
OH
ClCl
ClCl
10
O
ClCl
ClCl
O
Dess- Martinreagent
CH2Cl2 RT
O
Cl
ClCl
ClO
O
ClCl
ClCl
O
ClCl
Cl
Cl
OCl
ClCl
Cl
OCl
Cl
ClCl
toluene, rflx
13
14
15
DDQCH2Cl2
DDQCH2Cl2
9 (TCTD)
12
ORTEP plot of compound 12
intermediates towardtargets of type 6; wehave obtainedcrystal structures ofderivatives 3, 7 and 8.
Iso-Indenone Derivatives
