Open AccessCycloaddition reaction of phosphonyl nitrile oxides to phosphaacetylene and alkene
Author(s) -
Ye Yong,
Luo Yong,
Wang ChunFang,
Wei DongQing,
Liu LunZu,
Zhao YuFen
Publication year - 2009
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.20518
Subject(s) - nitrile , cycloaddition , chemistry , acrylonitrile , heteroatom , alkene , organic chemistry , medicinal chemistry , catalysis , ring (chemistry) , polymer , copolymer
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