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Volumn , Issue 18, 2008, Pages 2769-2772

Oxidation of primary amines to ketones

Author keywords

Amine; Benzoyl peroxide; Hydroxylamine; Ketone; Oxidation

Indexed keywords

AMINE; BENZOYL PEROXIDE; CARBONIC ACID DERIVATIVE; CESIUM; HYDROXYLAMINE; KETONE DERIVATIVE;

AIR; ARTICLE; CHEMICAL PARAMETERS; MOISTURE; OXIDATION; WARMING;

EID: 56849114610 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083541 Document Type: Article

Times cited : (17)

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- Typical Procedure for Conversion of N-Alkyl-O- benzoyl Hydroxylamines to Ketones: N-α-Methyl benzyl-O-benzoyl hydroxylamine (100 mg, 0.41 mmol) was dissolved in DMF (0.59 mL) at ambient temperature. Caesium carbonate (135 mg, 0.41 mmol) was added and the resulting reaction mixture was heated at 50°C overnight. The resulting reaction mixture was allowed to cool and purified directly by column chromatography, eluting with 20% EtOAc-PE, to give acetophenone (42 mg, 84, as a clear colourless oil. IR (thin film, 1683, 1599, 1582, 1449, 1359, 1266, 1180, 1078, 1025, 955, 760, 690 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.85 (d, J, 7.2 Hz, 2 H, 7.45 (t, J, 7.3 Hz, 1 H, 7.40-7.30 (m, 2 H, 2.50 (s, 3 H, 13C NMR (100 MHz, CDCl3, δ, 198.1, 137.1, 133.1, 128.6, 128.3, 26.6. MS EI, m/z, 120.06 [M, Typical Procedure for the One
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