Ring contraction of sulfenamides derived from thiochroman-4-ones

Christopher D. Gabbutt, John D. Hepworth, B. Mark Heron, Magan Kanjia

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Tiochroman-4-ones and chroman-4-ones react with an excess of thionyl chloride to give the α-chlorosulfenyl chlorides (2) which form sulfenamides (3) when treated with secondary amines. On hydrolysis, (3) undergo a ring contraction to give benzo[b]thiophen-3-ones (4).

Original languageEnglish
Pages (from-to)827-834
Number of pages8
JournalTetrahedron
Volume50
Issue number3
DOIs
Publication statusPublished - 17 Jan 1994
Externally publishedYes

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