Source: http://reag.paperplane.io/00000324.htm
Timestamp: 2019-04-23 06:02:56+00:00

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Physical Data: bp 137-139 °C, 78-80 °C/100 mmHg; d 0.830 g cm-3; flash point 28 °C.
Solubility: sol THF, ether, pentane, CH2Cl2.
Form Supplied in: liquid; widely available, but expensive.
Handling, Storage, and Precautions: flammable, corrosive liquid; hydrolyzed by moist air. Avoid inhalation and prevent contact with skin and eyes. The reagent should be stored under argon at 0-4 °C. Use in a fume hood.
Deprotonation of N,O-bis(trimethylsilyl)hydroxylamine with n-Butyllithium or Potassium Hydride at low temperature yields the nitrogen centered anion N,O-bis(trimethylsilyl)hydroxylamide.6,13 At higher temperatures the oxyanion N,N-bis(trimethylsilyl)hydroxylamide is formed by rearrangement.1,14 Each reacts with acyl chlorides chemospecifically by N-acylation and O-acylation, respectively. The oxyanion also reacts with silyl halides,1a methyl iodide,1 and sulfonyl chlorides14 chemospecifically on oxygen. In a Peterson-type one-pot reaction, oximes and oxime derivatives can be prepared effectively from the N-anion of N,O-bis(trimethylsilyl)hydroxylamine and an aldehyde or ketone (eq 5).13 Oximes of sterically hindered ketones can be formed in high yields by this procedure.
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12. (a) Harger, M. J. P.; Shimmin, P. A. TL 1991, 32, 4769. (b) Fawcett, J.; Harger, M. J. P.; Sreedharan-Menon, R. CC 1992, 227. (c) Harger, M. J. P.; Shimmin, P. A. T 1992, 48, 7539.
13. Hoffman, R. V.; Buntain, G. A. S 1987, 831.
14. King, F. D.; Walton, D. R. M. S 1975, 788.

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