Chemical and spectroscopical evidence for an electron‐transfer mechanism in the reaction of arenesulfonyl chlorides with anions | Zendy

Asensio Gregorio | Zendy; González Núñez Elena | Zendy; Rodrigo Maria José | Zendy; Varea Teresa | Zendy

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Chemical and spectroscopical evidence for an electron‐transfer mechanism in the reaction of arenesulfonyl chlorides with anions

Author(s) -

Asensio Gregorio,

González Núñez Elena,

Rodrigo Maria José,

Varea Teresa

Publication year - 1989

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19891220929

Subject(s) - chemistry , acylation , halide , electron transfer , amide , unpaired electron , acyl chloride , reaction mechanism , chloride , medicinal chemistry , photochemistry , organic chemistry , molecule , catalysis

The reaction of amide and amidate anions 2 with p ‐toluenesulfonyl chloride ( 1 ) under different reaction conditions gives rise to the total or partial reduction of the acyl halide to p ‐toluenesulfinic acid ( 5 ) and acylation compounds in variable amounts depending on the crowding at the anionic center. This indicates that a Single‐Electron Transfer (SET) mechanism is involved in the reactions of 1 with anions. Unpaired electron species are detected by ESR in the course of the reactions.

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