Journal of the American Chemical Society

Alkynyl sulfenylation. A direct approach for nucleophilic addition and substitution of olefins by carbanions

BM Trost, SJ Martin

Index: Trost, Barry M.; Martin, Steven J. Journal of the American Chemical Society, 1984 , vol. 106, # 15 p. 4263 - 4265

Full Text: HTML

Citation Number: 35

Abstract

Eliminations were accomplished either by oxidation to the sulfoxide followed by heating in a sealed tube at 140-220" C (CaC03, C2H50CH= CH2) 9 [eq 6 and 7 (14a: 14b 2: 1)] or by alkylationelimination [CF3S03CH2C02C2H5, CH3CN then DBU'O eq 5, 7 (14a: 14b 5: 1), and 81. Since both eliminations are known to be cis, the elimination products provide chemical evidence for the stereochemistry of the alkynyl sulfenylation. The versatility of ...