Decomposition of N-cyclopropyl-N-nitrosourea in the presence of reducing agents as a new way of generating the cyclopropyl radical

Abstract

A new way of generating cyclopropyl radicals in the base catalyzed decomposition of N cyclopropyl N nitrosourea in the presence of organic reducing agents (1 phenylpyrazolidin 3 one and 4 methoxyphenol) was developed. The cyclopropyl radical generated under these conditions can not only abstract a proton from the substrate to give cyclopropane but also form C-C or C-Br bonds in reactions with aromatic substrates or polybromomethanes.

Azo-coupling and reduction of cyclopropanediazonium ions in the reactions with polyhydroxyarenes and aminophenols

“…), but also by the direct observation of the chemical nuclear polariza tion effect for the signal of cyclopropane when the reaction was carried out directly in the detector of an NMR spec trometer. 4 In particular, it was found that decomposition of nitrosourea 1a under action of cesium carbonate in the presence of 4 methoxyphenol leads to the formation of three major compounds, viz., 2 (cyclopropylazo) 4 methoxyphenol, cyclopropane, and allene in the molar ratio of ~1.6 : 1.8 : 1.0.…”