Multiple reactivity of freund's “methyl isothiocyanate sulfide” in cycloaddition‐elimination reactions | Zendy

L'Abbé Gerrit | Zendy; Sannen Ingrid | Zendy; Vandendriessche Ann | Zendy

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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 .

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