Synlett

Aromatic ring opening of fused thiophenes via organolithium addition to sulfur

B Hill, M De Vleeschauwer, K Houde, M Belley

Index: Hill; De Vleeschauwer; Houde; Belley Synlett, 1998 , # 4 p. 407 - 410

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Citation Number: 7

Abstract

While working on thieno[3,2-d]thiazole 11, we encountered an unexpected reaction. Treatment of 1 with butyllithium at -100°C and addition of N-chlorosuccinimide yielded a product containing a butyl group and an extra chlorine atom. This unknown compound was then oxidized to the sulfone 4, which was identified by X-ray crystallography (scheme 1 and figure 1). This addition product could be explained by the addition reaction of the butyl group to the sulfur atom of ...