Photochemical Nitration by Tetranitromethane. XIV. The Formation of 1,3-Dipolar Nitro Addition Products From the Photochemical Reaction of 1,2-Dimethylnaphthalene and Tetranitromethane

Abstract

Photolysis of the 1,2-dimethylnaphthalene/tetranitromethane charge-transfer complex yields the triad of 1,2-dimethylnaphthalene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad gives predominantly the adducts (13)-(16), each of which is formed by attack of the trinitromethanide ion at C4 of the 1,2-dimethylnaphthalene radical cation. Thermal cycloaddition in adducts (13) and (16) gives the cycloadducts (12) and (17) respectively.