Generation of Phthalimido-Nitrene and its Reactions

Abstract

Depending on the reaction conditions, the oxidation of N-amino-phthalimide (1) with lead tetraacetate gave variable amounts of phthalimide (2) and of another product for which the structure of 1,4-bis-phthalyl-tetrazene (6) is proposed. A possible mechanistic scheme accounting for the products and the effects is discussed. A singlet character of the intermediate phthalimido-nitrene (4) is suggested by the stereospecific addition onto cis- and trans-butenes and by the exclusive 1,2-addition onto cyclohexa-1,3-diene.