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Chemical investigations of citraconimide
Author(s) -
Earl Robert A.,
Clough Fred W.,
Townsend Leroy B.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150846
Subject(s) - chemistry , steric effects , regioselectivity , reactivity (psychology) , double bond , alkyl , organic chemistry , medicinal chemistry , computational chemistry , catalysis , medicine , alternative medicine , pathology
The chemical reactivity of citraconimide (3‐methylmaleimide, 2 ) has been investigated with special emphasis being placed on the use of mild and selective reaction conditions. Particular attention has been focused on the theiotropic reactivity of citraconimide. The results indicate that the reaction of various mercaptans with citraconimide is highly regioselective resulting predominately in the geminally substituted products with the percentage of vicinally substituted products increasing as a function of the steric bulk of the alkyl mercaptan. Additional studies on the double bond of citraconimide have furnished 4‐halogeno‐ and the 3,4‐dihydro derivatives of citraconimide. Several N ‐substituted citraconimide derivatives have also been prepared.