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Cycloaddition‐elimination reactions of 4‐methyl‐5‐phenylimino‐Δ 2 ‐1,2,3,4‐thiatriazoline with electrophilic nitriles
Author(s) -
L'abbé Gerrit,
Sannen Ingrid
Publication year - 1991
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.5570280223
Subject(s) - chemistry , cycloaddition , chloroform , electrophile , acetone , medicinal chemistry , solvent , decomposition , cyanide , organic chemistry , catalysis
4‐Methyl‐5‐phenyliminothiatriazoline 4 undergoes two consecutive cycloaddition‐elimination reactions with ethyl cyanoformate and p ‐toluenesulfonyl cyanide in refluxing chloroform, and yields the 1,2,4‐thiadiazolines 6a,b via the isomers 5a,b . In acetone as the solvent, the reactions occur at room temperature, due to the formation of the 1,2,4‐oxathiazolidine 12 as the intermediate. When trichloroacetonitrile was used, only the decomposition products of 4 , namely 7 and 8 were obtained.