The sulfohaloform reaction. The stepwise conversion of dialkyl sulfides into alkanesulfonyl chlorides
作者:
J. Stuart Grossert,
Richard F. Langler,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1977)
卷期:
Volume 55,
issue 3
页码: 407-420
ISSN:0008-4042
年代: 1977
DOI:10.1139/v77-061
出版商: NRC Research Press
数据来源: NRC
摘要:
A thorough examination of the aqueous oxidative chlorination of 1,3,5-trithiane is described. The results are utilized to explore and delineate the scope of a general, stepwise, oxidative cleavage reaction of dialkyl sulfides in which they are successively halogenated and oxidized to α-polychlorosulfoxides; subsequently, these cleave to form sulfinyl chlorides, which hydrolyze and become further oxidized to yield alkanesulfonyl chlorides. The overall stepwise process is named the 'Sulfohaloform reaction' and the structural requirements of the substrates at each step are explored in detail. A practical, general synthesis of sulfonyl chlorides is presented.
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