Abstract
A range of N -alkyl imines was oxidised to corresponding oxaziridines in a highly selective manner with sodium tungstate-30% H2 O2 in acetonitrile under mild conditions.
Key words
imines - oxidation - oxaziridine - sodium tungstate - peroxide
References
1 Krimm H.
Chem. Ber.
1957,
91:
1057
2 Emmons WD.
J. Am. Chem. Soc.
1956,
78:
62089
3 Horner L.
Jurgens E.
Chem. Ber.
1957,
90:
2184
4a Davis FA.
Sheppard AC.
J. Org. Chem.
1987,
52:
954
4b Davis FA.
Billmers RH.
J. Am. Chem. Soc.
1981,
103:
7016
5a Andreae S.
Schmitz E.
Synthesis
1991,
327
5b Armstrong A.
Atkin MA.
Swallow S.
Tetrahedron Lett.
2000,
41:
2247
5c Bohe L.
Lusinchi X.
Tetrahedron
1999,
55:
155
5d Jennings WB.
Oshea JH.
Schweppe A.
Tetrahedron Lett.
2001,
42:
101
6 Davis FA.
Sheppard AC.
Tetrahedron
1989,
45:
5703
7a Davis FA.
Jenkins RH. In Asymmetric Synthesis
Vol. 4:
Morrison JD.
Academic Press;
New York:
1984.
Chap. 4.
p.7
7b Aube J.
J. Chem. Soc. Rev.
1997,
26:
269
7c Davis FA.
Chen B.-C.
Chem. Rev.
1992,
92:
919
8 Peng L.
Chen C.
Gonzalez CR.
Balogh-Nair V.
Int. J. Mol. Sci.
2002,
3:
1145
9a Pews RG.
J. Org. Chem.
1967,
32:
1628
9b Davis FA.
Stringer OD.
J. Org. Chem.
1982,
47:
1774
9c Boyd DR.
Jennings WB.
McGuckin RM.
Rutherford M.
Saket BM.
J. Chem. Soc., Chem. Commun.
1985,
582
9d Kloc K.
Kubicz E.
Mlochowski J.
Syper L.
Synthesis
1987,
1084
9e Joelle V.
Stephanie D.
Laure G.
Andre HJ.-CA.
Andre C.
Chem.-Eur. J.
1997,
3:
1691
10 Emmons WD.
J. Am. Chem. Soc.
1957,
79:
5739
11 Asgarian Damvandi J.
Kavami B.
Zoltigol MA.
Synlett
2002,
933
12a Schirmann J.-P.
Weiss F.
Tetrahedron Lett.
1972,
633
12b Kraiem J.
Kacem Y.
Khiari J.
Hassine B.
Synth. Commun.
2001,
31:
263
13a Davis FA.
Chattopadhya S.
Towson JC.
Lal S.
Reddy T.
J. Org. Chem.
1988,
53:
2087
13b Hajipour AR.
Pyne SG.
J. Chem. Res., Synop.
1992,
388
14 Tolstikov GA.
Jemilev UM.
Jurjev VP.
Gershnov FB.
Rafikov SR.
Tetrahedron Lett.
1971,
2807
15a Auret BJ.
Boyd DR.
Coulter PB.
J. Chem. Soc., Chem. Commun.
1984,
463
15b Martiny L.
Jorgenson KA.
J. Chem. Soc., Perkin Trans. 1
1995,
699
16
General Procedure.
2 O2 (0.15 mL) dropwise at r.t. The progress of the reaction was monitored by TLC. After the completion of the reaction, the solvent was removed in vacuo, any excess H2 O2 was quenched with sat. Na2 SO3 solution and the product was re-extracted with CHCl3 . The solvent was dried over Na2 SO4 (anhyd) and evaporated. The crude product was purified by column chromatography on silica gel using mixtures of hexane and EtOAc.
