Rubber, Polyisoprenes, and Allied Compounds. VII. Action of Nitric Oxide

The reaction of nitric oxide with the olefins cyclohexene, 1-methylcyclohexene, dihydromyrcene, and rubber presents characteristics of a free-radical, chain reaction. In the products, the molecular ratio of combined oxygen to nitrogen is considerably in excess of 1:1, the nitrogen atom being generally directly linked to carbon. In many instances definite nitro compounds have been isolated, and a considerable part of the attack appears to proceed at the ethylenic carbon atoms, either by substitution or addition of NO2 and N2O3 groups. The precise reaction mechanism is obscure.