The chlorosulfonyl moiety as a leaving group: hydride reduction of sulfonyl chlorides

A series of γ-sulfone sulfonyl chlorides undergo a novel reduction upon reaction with lithium aluminum hydride to furnish the corresponding ethyl sulfones. The reactions appear to proceed in an S N 2 fashion with the chlorosulfonyl moiety functioning as the leaving group. In general sulfonyl chlorid...

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Bibliographic Details
Published in:Canadian journal of chemistry 1979-05, Vol.57 (10), p.1206-1213
Main Authors: Fong, Harvey Owen, Hardstaff, William Rayne, Kay, Denis George, Langler, Richard Francis, Morse, Richard Herman, Sandoval, Deig-Nevy
Format: Article
Language:English
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Summary:A series of γ-sulfone sulfonyl chlorides undergo a novel reduction upon reaction with lithium aluminum hydride to furnish the corresponding ethyl sulfones. The reactions appear to proceed in an S N 2 fashion with the chlorosulfonyl moiety functioning as the leaving group. In general sulfonyl chlorides furnish mercaptans as hydride reduction products.A novel two-phase hydrolysis is shown to convert a thiol ester to a symmetric sulfide which involves hydrolysis and an S N 2 displacement in the aqueous phase.
ISSN:0008-4042
1480-3291
DOI:10.1139/v79-196