Ring contraction of sulfenamides derived from thiochroman-4-ones

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

doi:10.1016/S0040-4020(01)80797-3

Ring contraction of sulfenamides derived from thiochroman-4-ones

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	827-834
Number of pages	8
Journal	Tetrahedron
Volume	50
Issue number	3
DOIs	https://doi.org/10.1016/S0040-4020(01)80797-3
Publication status	Published - 17 Jan 1994
Externally published	Yes

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title = "Ring contraction of sulfenamides derived from thiochroman-4-ones",

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).",

author = "Gabbutt, {Christopher D.} and Hepworth, {John D.} and Heron, {B. Mark} and Magan Kanjia",

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AU - Gabbutt, Christopher D.

AU - Hepworth, John D.

AU - Heron, B. Mark

AU - Kanjia, Magan

PY - 1994/1/17

Y1 - 1994/1/17

N2 - 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).

AB - 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).

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U2 - 10.1016/S0040-4020(01)80797-3

DO - 10.1016/S0040-4020(01)80797-3

M3 - Article

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SN - 0040-4020

VL - 50

SP - 827

EP - 834

JO - Tetrahedron

JF - Tetrahedron

IS - 3

ER -

Ring contraction of sulfenamides derived from thiochroman-4-ones

Abstract

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