Chemistry Letters

Regio-and stereo-selective oxidation of gem-dimethyl olefins via [2, 3]-sigmatropic rearrangement of allyl amine oxides

S Inoue, N Iwase, O Miyamoto, K Sato

Index: Inoue, Seiichi; Iwase, Norimichi; Miyamoto, Osamu; Sato, Kikumasa Chemistry Letters, 1986 , p. 2035 - 2038

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Citation Number: 18

Abstract

2036 Chemistry Letters, 19 8 6 3) led to fewer amount of by-products, hence resulted 4) cribed in the original paper in higher yield of 3d. Subsequent [2,3]-sigmatropic rearrangement4'' was carried out by oxidation of allylamines 3 with peracetic acid followed by heating the crude allylamine oxides 4. Peracetic acid (40%; 1.0 g; 5.5 mmol) was added dropwise to a mixture of 3 (5.0 mmol) and solid Na2C03 (0.6 g; 5.5 mmol) in CH2C12 (50 ml) at -50 °C with vigorous ...