
%0 Journal Article
%A Poppinger, D 
%T <I>Ab initio</I> molecular orbital study of simple 1,3-dipolar reactions
%J Australian Journal of Chemistry
%D 1976/03/01
%V 29
%N 3
%P 465-478
%K 
%R https://doi.org/10.1071/CH9760465
%U https://www.publish.csiro.au/paper/CH9760465 
%X Ab initio molecular orbital calculations with minimal and extended basis sets have been carried out for the 1,3-dipolar addition of fulminic acid to acetylene, ethylene, ethynamine and propynenitrile. Optimized geometries are reported for the transition states HCNO+C2H2, HCNO+C2H4, HCNO+ C2HNH2, for the adducts isoxazole and 2-isoxazoline, and for nitrosocyclopropene as a possible intermediate. The calculations indicate that (a) these 1,3-dipolar reactions are synchronous processes, (b) the geometry of the transition state is insensitive to substitution and (c) of the isomeric substituted adducts, 5-aminoisoxazole and isoxazole-4-carbonitrile should be formed preferentially. 
