Nitrosation of the N-Alkyl-O-acylhydroxylamines. A New Deamination Method.

Article abstract of DOI:10.1021/jo00199a024

The nitrosation of N-alkyl-O-acylhydroxylamines leads to immediate decomposition at dry ice temperatures; the corresponding ester and nitrous oxide are formed.An 18O study has shown that the nitroso-O-acylhydroxylamines fragment directly rather than undergo a rearrangement reaction (as observed with the nitrosoamides).The product yields are respectable, especially at low tempreatures, and the method has promise for the generation of high energy carbonium ions.