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

University of Lancashire

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

Access to Document

10.1016/S0040-4020(01)80797-3Licence: Unspecified

Cite this

@article{1fa8e3d1513f4068870aa6e177bec5ab,

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",

year = "1994",

month = jan,

day = "17",

doi = "10.1016/S0040-4020(01)80797-3",

language = "English",

volume = "50",

pages = "827--834",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "3",

}

TY - JOUR

T1 - Ring contraction of sulfenamides derived from thiochroman-4-ones

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).

UR - https://www.scopus.com/pages/publications/0027972570

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

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

M3 - Article

AN - SCOPUS:0027972570

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

Access to Document

Other files and links

Fingerprint

Cite this