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Multiple reactivity of freund's “methyl isothiocyanate sulfide” in cycloaddition‐elimination reactions
Author(s) -
L'Abbé Gerrit,
Sannen Ingrid,
Vandendriessche Ann
Publication year - 1992
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.5570290111
Subject(s) - chemistry , electrophile , thiazole , thiourea , isothiocyanate , cycloaddition , isocyanate , imine , sulfide , carbon disulfide , medicinal chemistry , reactivity (psychology) , acetone , organic chemistry , catalysis , medicine , alternative medicine , pathology , polyurethane
4‐Methyl‐5‐methylimino‐1,2,4‐dithiazolidine‐3‐thione ( l )and 2,4‐dimethyl‐1,2,4‐thiadiazolidine‐3,5‐dithione ( 2 ) are interconvertible in acetone at 50°. They react with ketenes and electrophilic acetylenes to give the thiazole derivatives 6 and 7 after elimination of methyl isothiocyanate or carbon disulfide. Electrophilic isothiocyanates and phenylsulfonyl isocyanate transform the C = S function of 1 in an imine function ( 8 ), and a similar transformation of the thiourea C = S function of 2 is observed on reaction with phenylsulfonyl isocyanate, giving 9 .