A new reaction of α-chloro-α-chlorosulfenyl ketones: facile syntheses of 3,3-dichloro- and 3-chloro-chroman-4-ones and thiochroman-4-ones

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Abstract

3-Chloro-3-chlorosulfenylchroman-4-ones are efficiently obtained from chroman-4-ones by treatment with thionyl chloride. Direct oxidation affords 3,3-dichlorochroman-4-ones, whilst conversion to the sulfenamides prior to oxidation provides a facile route to 3-chlorochroman-4-ones.

LanguageEnglish
Pages5245-5254
Number of pages10
JournalTetrahedron
Volume50
Issue number17
DOIs
Publication statusPublished - 25 Apr 1994
Externally publishedYes

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Chromans
Ketones
Oxidation
sulfenamide
thionyl chloride

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title = "A new reaction of α-chloro-α-chlorosulfenyl ketones: facile syntheses of 3,3-dichloro- and 3-chloro-chroman-4-ones and thiochroman-4-ones",
abstract = "3-Chloro-3-chlorosulfenylchroman-4-ones are efficiently obtained from chroman-4-ones by treatment with thionyl chloride. Direct oxidation affords 3,3-dichlorochroman-4-ones, whilst conversion to the sulfenamides prior to oxidation provides a facile route to 3-chlorochroman-4-ones.",
author = "{D. Gabbutt}, Christopher and {D. Hepworth}, John and {Mark Heron}, B.",
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AU - D. Hepworth, John

AU - Mark Heron, B.

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N2 - 3-Chloro-3-chlorosulfenylchroman-4-ones are efficiently obtained from chroman-4-ones by treatment with thionyl chloride. Direct oxidation affords 3,3-dichlorochroman-4-ones, whilst conversion to the sulfenamides prior to oxidation provides a facile route to 3-chlorochroman-4-ones.

AB - 3-Chloro-3-chlorosulfenylchroman-4-ones are efficiently obtained from chroman-4-ones by treatment with thionyl chloride. Direct oxidation affords 3,3-dichlorochroman-4-ones, whilst conversion to the sulfenamides prior to oxidation provides a facile route to 3-chlorochroman-4-ones.

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EP - 5254

JO - Tetrahedron

JF - Tetrahedron

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