Nitrones and oxaziridines. VIII. Cycloaddition reactions of nitrones with isothiocyanates

Abstract

Whereas nitrones undergo cycloaddition to the C=N double bond of phenyl isothiocyanate, predominant addition to the C=S double bond of substituted phenyl isothiocyanates, methyl isothiocyanate and benzoyl isothiocyanate occurs. However, these cycloadducts are not stable but undergo fragmentation usually with the formation of thioamides and isocyanates.