Tetrahedron letters

Regioselectivity in the 1, 3-dipolar cycloaddition of nitrile oxides to alkylidenecyclopropanes.

A Brandi, S Carli, A Guarna, F De Sarlo

Index: Brandi, Alberto; Carli, Silvio; Guarna, Antonio; Sarlo, Francesco De Tetrahedron Letters, 1987 , vol. 28, # 33 p. 3845 - 3848

Full Text: HTML

Citation Number: 10

Abstract

Abstract The 1, 3-dipolar cycloaddition of nitrile oxides to methylenecyclopropanes substituted on the exocyclic double bond gives prevalently or exclusively 4- spirocyclopropane isoxazolines when the substituent is arylic or alkylic group, 5- spirocyclopropane isoxazolines when the substituent is an electron-withdrawing group. Adducts 16 and 17 selectively rearrange photochemically to the enaminoenone 19.