Synthesis and Decomposition of the N-Alkyl-N-nitro-O-benzoylhydroxylamines

Article abstract of DOI:10.1021/jo00199a025

Nitration of N-alkyl-O-benzoylhydroxylamines yields the correspondng N-nitro derivatives.At modest temperatures these compounds decompose to yield alkyl benzoates, alkenes, benzoic acid, and nitrous oxide.In the case of primary alkylnitrohydroxylamines, nitroalkanes and alkyl nitrates are also formed.The alkyl benzoates are products of ionic reactions since skeletal rearrangements characteristics of carbonium ions occur.The insensivity of the rates of decomposition to solvent polarity suggests that the rate-determining step is a rearrangement rather than direct ionization.