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Synthetic applications of 3,4-bis(trimethylsilyl)thiophene: unsymmetrically 3,4-disubstituted thiophenes and 3,4-didehydrothiophene

Authors :
Ye, Xin-Shan
Wong, Henry N.C.
Source :
Journal of Organic Chemistry. April 4, 1997, Vol. 62 Issue 7, p1940, 15 p.
Publication Year :
1997

Abstract

A novel method for the synthesis of unsymmetrically 3,4-disubstituted thiophenes was developed based on the intermolecular thiazole-alkyne Diels-Alder reactions involving 3,4-bis(trimethylsilyl)thiophene. The synthetic strategy was characterized by the formation of the [2+2]- and [4+2]-cycloaddition adducts of 3,4-didehydrothiophene via 1,3-dipolar cycloadditions. Furthermore, the synthetic process was characterized by 3,4-bromothiophene modification and intermolecular thiazole-alkyne Diels-Alder reactions with 3,4-bis(trimethylsilyl)thiophene.

Details

ISSN :
00223263
Volume :
62
Issue :
7
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.19736420