Cycloaddition reaction of phosphonyl nitrile oxides to phosphaacetylene and alkene

Abstract

Abstract Here, we report the cycloaddition reaction of phosphonyl nitrile oxides and the formation of an unexpected 2:1 cycloaddition product. It provides a direct route to triphosphonyl‐substituted dihydroisoxazolyl dihydroisoxazoles and diphosphonyl‐substituted dihydroisoxazolyl dihydroisoxazoles with excellent levels of regiocontrol product. Density functional theory studies of the reactions between nitrile oxides and acrylonitrile are used to propose a possible reaction mechanism. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:95–100, 2009; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20518