Synthesis and Decomposition of Functionalized Diaziridinimines

Article abstract of DOI:10.1021/jo00335a031

The conversion of guanidines into diaziridinimines on treatment with t-BuOCl and t-BuOK can be applied to the synthesis of sulfonyl-, phosphoryl-, and cyano-substituted derivatives bearing two additional tert-butyl groups.Carbethoxy- and benzoyl-substituted guanidines give N-carbonyl-substituted diaziridinimines only as elusive intermediates which rearrange into 5-imino-Δ²-1,3,4-oxadiazolines.Other decomposition pathways observed are (i) rearrangement of sulfonylimino- and phosphorylimino-substituted diaziridines into hydrazine derivatives and (ii) cheletropic decomposition of N-cyano-substituted diaziridinimines into carbodiimides and cyanonitrene.