Hydroxylamine reaction with acyl halides

In a similar reaction, aromatic acyl halides are converted to amines in one laboratory step by treatment with hydroxylamine-O-sulfonic acid. " ... 

Allylation of acyloyl-imidazoles and pyrazoles61 with allyl halide mediated by indium in aqueous media provides a facile regioselective synthesis of P, y-unsaturated ketones (Scheme 11.1), which has been applied to the synthesis of the monoterpene artemesia ketone. The same product can be obtained by indium-mediated allylation of acyl cyanide (Eq. 11.35).62 Samarium, gallium, and bismuth can be used as a mediator for the allylation of nitrones and hydrazones to give homoallylic hydroxylamine and hydrazides in aqueous media in the presence of Bu4NBr (Scheme 11.2).63 The reaction with gallium and bismuth can be increased dramatically under microwave activation. 

Deprotonation of Al,<9-bis(trimethylsilyl)hydroxylamine with n-butyllithium or potassium hydride at low temperature yields the nitrogen centered anion Al,<9-bis(trimethylsilyl)hydroxyl-amide. At higher temperatures the oxyanion Al,A -bis(tri-methylsilyl)hydroxylamide is formed by rearrangement. Each reacts with acyl chlorides chemospecifically by M-acylation and 0-acylation, respectively. The oxyanion also reacts with silyl halides, methyl iodide, and sulfonyl chlorides chemospecifically on oxygen. In a Peterson-type one-pot reaction, oximes and oxime derivatives can be prepared effectively from the N-anion of iV,0-bis(trimethylsilyl)hydroxylamine and an aldehyde or ketone (eq 5). Oximes of sterically hindered ketones can be formed in high yields by this procedure. 

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