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40.5.2.1.1.2 Method 2: Synthesis from O-Alkyl Hydroxamates

DOI: 10.1055/sos-SD-040-00666

Geffken, D.; Köllner, M. A.Science of Synthesis, (2009401006.

Alkylation of free hydroxamic acids in the presence of a base occurs preferentially at the nitrogen-bonded oxygen atom to give O-alkyl hydroxamates (N-alkoxyamides), which can be hydrolyzed with acid or base to give O-alkylhydroxylamines.[‌449‌‌453‌] Alkylation of benzohydroxamic acid followed by hydrolysis, provides access to a variety of O-alkyl- and O-(arylalkyl)hydroxylamines, e.g. 4-nitrobenzyloxyamine, ethoxyamine, propoxyamine, isopropoxyamine, and allyloxyamine, in modest to good yields.[‌454‌]

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