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Synlett 2002(6): 0933-0934
DOI: 10.1055/s-2002-31903
LETTER
© Georg Thieme Verlag Stuttgart · New York

Selective Oxidation of N-Alkyl Imines to Oxaziridines using UHP/Maleic Anhydride system

Jafar Asgarian Damavandia, Bahador Karamia, Mohammad Ali Zolfigol*b
a Faculty of Chemistry, University of Teacher Training, Tehran, I. R. Iran
b Chemistry Department, College of Science, Bu-Ali Sina University, Hamadan, Zip Code 65174, Post Box No. 4135, I. R. Iran
e-Mail: Zolfi@basu.ac.ir;
Further Information

Publication History

Received 28 February 2002
Publication Date:
07 February 2007 (online)

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Abstract

Several structurally differentiated N-alkyl imines were oxidized to their corresponding oxaziridines using UHP/maleic anhydride system. Oxidation reaction was performed under mild conditions and oxaziridines were obtained in good to excellent yields.

Key words

UHP - N-alkyl imines - oxaziridines

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Yields refer to isolated pure products. The oxidation products were characterized by comparison of their spectral (IR, 1H NMR, and 13C NMR) and physical data with the authentic samples.

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Oxidation of N-benzylphenyl imine(1a) to 2-benzyl-3-phenyl oxaziridine(2a) with UHP/maleic anhydride system. A typical procedure: A suspension of compound 1a (0.390 g, 2 mmol), I (0.188 g, 2 mmol), maleic anhydride (0.176 g, 2 mmol) in methanol (8 mL) was stirred at 0 °C. The progress of the reaction was monitored by TLC (eluent, EtOAc-n-hexane, 1:5). The reaction was completed after 40 min. The reaction mixture was filtered and the filtrate was passed through a short pad of silica gel. Methanol was removed under reduced pressure. Highly pure oxaziridine(2a) was obtained in 95% yield (0.354 g). (FT-NMR 500 MHz) CDCl3: δppm 4.03-4.22 (dd, 2 H), 4.8 (s, 1 H), 7.45-7.6 (m, 10 H). [7a]