The Journal of Organic Chemistry

1, 3-Dipolar cycloadditions of nitrones derived from the reaction of acetylenes with hydroxylamines

A Padwa, GSK Wong

Index: Padwa, Albert; Wong, George S. K. Journal of Organic Chemistry, 1986 , vol. 51, # 16 p. 3125 - 3133

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Citation Number: 86

Abstract

A study of the reaction of hydroxylamines with a variety of acetylenes has been carried out. Methylhydroxylamine readily reacts with methyl propiolate to give methyl 4-carbomethoxy-2- methyl-4-isoxazolidine-3-acetate. Further heating of this material results in the formation of N- methyl-2, 4-dicarbomethoxypyrrole by a mechanism which involves homolysis of the 0-N linkage. The transient aziridine which is suggested to be formed reacts further to give the ...