INSERTION OF BENZOYLNITRENE TOWARD HYDROCARBON C-H BONDS

Article abstract of DOI:10.1246/cl.1981.1419

Benzoylnitrene, generated photochemically from benzoyl azide, was inserted stereospecifically into the tertiary C-H bonds of cis- and trans-1,4-dimethylcyclohexanes.The insertion regioselectivities toward the C-H bonds were determided by use of 2-methylbutane and 2,3-dimethylbutane.The insertion proceeds involving the singlet nitrene, but not the triplet, and the photoCurtius rearrangement takes place independently of the nitrene reaction.