PHOTOCHEMICAL NITRATION BY TETRANITROMETHANE .14. THE FORMATION OF 1,3-DIPOLAR NITRO ADDITION-PRODUCTS FROM THE PHOTOCHEMICAL-REACTION OF 1,2-DIMETHYLNAPHTHALENE AND TETRANITROMETHANE

Photolysis of the 1,2-dimethylnaphthalene/tetranitromethane charge-tra nsfer complex yields the triad of 1,2-dimethylnaphthalene radical cati on, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad gives predominantly the adducts (13)-(16), each of which is for med by attack of the trinitromethanide ion at C4 of the 1,2-dimethylna phthalene radical cation. Thermal cycloaddition in adducts (13) and (1 6) gives the cycloadducts (12) and (17) respectively.