N-NITROSOHYDROXYLAMINES I. ACETOLYSIS AND ACID-CATALYZED HYDROLYSIS OF N,O-DIBENZYL-N-NITROSOHYDROXYLAMINES. REACTION WITH POTASSIUM t-BUTOXIDE

Article abstract of DOI:10.1016/S0040-4020(01)89037-2

The major products of the hydrolysis of N,O-dibenzyl-N-nitrosohydroxylamines (3) are the denitrosated parent hydroxylamines (6); under more forcing conditions, products of the further hydrolysis of 6 are obtained.Acetolysis in acetic acid gives the benzyl acetates derived from both N- and O-substituents.With potassium tert-butoxide, the major path is abstraction of an O-benzyl hydrogen followed by fragmentation to the aldehyde and the benzyldiazotate ion.Possible mechanisms for the formation of the products are discussed.