Reduction of Azoalkanes by Benzhydryl Radicals

Article abstract of DOI:10.1021/ja00187a043

Benzhydryl radicals donate a hydrogen atom rapidly to the less hindered nitrogen atom of aliphatic and aromatic azo compounds, leading to the corresponding hydrazines.When the initially formed hydrazyl radical posseses a weak β-bond, it undergoes scission before receiving a second hydrogen atom.Thermolysis of benzpinacol with azocyclopropane causes a complex rearrangement to 1,5-diazaoct-5-en-1-yne (21).