The reaction of primary nitro compounds with dipolarophiles in the presence of p-toluenesulfonic acid.

T Shimizu, Y Hayashi, K Teramura

Index: Shimizu; Hayashi; Teramura Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 9 p. 2531 - 2534

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Citation Number: 41

Abstract

3-Substituted 2-isoxazolines or isoxazoles were obtained from the reaction of primary nitro compounds [methyl nitroacetate, 2-nitro-1-phenylethanone,(nitromethyl) benzene, 1- nitropropane, and (phenylsulfonyl) nitromethane] with dipolarophiles in refluxing mesitylene in the presence of a small amount of p-toluenesulfonic acid. The formation of these products can be explained in terms of 1, 3-dipolar cycloaddition of nitrile oxide generated by a ...