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Cycloaddition-Elimination Reactions of 4-Methyl-5-phenylimino-Δ2-1,2,3,4-thiatriazoline with Electrophilic Nitriles
L'abbe, Gerrit,Sannen, Ingrid
, p. 333 - 336 (2007/10/02)
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.
