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Title: New highly efficient method for the synthesis of tert-alkyl nitroso compounds
Authors: Quek, S.K.
Lyapkalo, I.M.
Huynh, H.V. 
Keywords: Benzoyl peroxide
Selective oxidation
Steric hindrance
Tert-alkyl amines
Tert-alkyl nitroso compounds
Issue Date: 3-May-2006
Citation: Quek, S.K., Lyapkalo, I.M., Huynh, H.V. (2006-05-03). New highly efficient method for the synthesis of tert-alkyl nitroso compounds. Synthesis (9) : 1423-1426. ScholarBank@NUS Repository.
Abstract: The syntheses of tert-alkyl nitroso compounds RCH2CMe 2N=O from commercially available tert-alkyl amines RCH 2CMe2NH2 proceed cleanly via the intermediacy of the benzoyl derivatives RCH2CMe2NHOC(O)Ph and the corresponding hydroxylamines RCH2CMe2NHOH. Since the intermediates require no purification in the course of the transformations, the overall yields of the isolated crystalline nitroso dimers (75-80% for R = H, 75% for R = Me and 66% for R = Me3C) are based on the corresponding amine precursors. In the latter case (R = Me3C), significant steric demands and hydrophobicity of Me3CCH2CMe2 group necessitate the application of more efficient reagents and conditions on the debenzoylation and oxidation steps. The syntheses are perfectly suitable for scale-up and were successfully performed on up to 500-mmol scale. © Georg Thieme Verlag Stuttgart.
Source Title: Synthesis
ISSN: 00397881
DOI: 10.1055/s-2006-926442
Appears in Collections:Staff Publications

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