Collect. Czech. Chem. Commun. 1991, 56, 1167-1172

MNDO study of the [2 + 3] cycloaddition of nitroethene to formonitrile N-oxide

Andrzej Barański and Jerzy Cioslowski

Institute of Organic Chemistry and Technology, Technical University, 31-155 Cracow, Poland


Two regioisomeric pathways have been studied by MNDO method for nitroethene [2 + 3] cycloaddition to formonitrile N-oxide. It has been found that four critical structures are located along each of the pathways. Calculations indicate that both reactions take place in a concerted manner and that their transition states are early. Moreover, it was established that the path leading to 5-nitro-4,5-dihydro-1,2-oxazole is preferred.