Journal of the Chemical Society. Perkin transactions I p. 1629 - 1633 (1996)
Update date:2022-08-28
Topics:
Tornus, Ingo
Schaumann, Ernst
Adiwidjaja, Gunadi
Reaction of 3-dimethylamino-2,2-diphenyl-2H-azirine 3a with N-sulfonylalkylamines 2a,b provides 1,2,5-thiadiazoles 5a,b, whereas use of N-carbonylsulfonylamines 2c,e as reaction partners primarily results in 1,2,3-oxathiazoles 6a,b which isomerise to the corresponding thiadiazoles 5c,d on treatment with silica gel at room temperature. In contrast, use of 2-alkyl-3-dimethylamino-2-phenyl-2H-azirines 3b,c in the reaction with the N-sulfonylamide 2c and the N-sulfonylcarbamates 2e,f leads to mixtures of thiadiazoles 5 and oxathiazoles 6 along with isomeric acrylamidines 7.
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