Attempted cycloaddition of N-ethoxycarbonylmethylenenamine to N-ethoxycarbonylazepine: formation of 4,4′-bis(ethoxycarbonylamino)-diphenylmethane

Abstract

Three products were formed in the boron trifluoride-catalysed reaction of N-ethoxycarbonylmethyleneamine with N-ethoxycarbonylazepine, N-ethoxycarbonylaniline (2), 4-(N-ethoxycarbonylaminomethyl)-N-ethoxycarbonylaniline (3), and 4,4′-bis-(N-ethoxycarbonylamino)diphenylmethane (4). Product (4) was independently synthesised. The mechanisms of formation of the products (2), (3), and (4) were established.