The synthesis and some reactions of 1,2,2-trimethylbicyclobutane

1,2,2-Trimethylbicyclo[1.1.0]butane reacted with excited state 1-cyanonaphthalene at a diffusion-controlled rate in methanol to produce cis- and trans-1-methoxy-2,2,3-trimethylcyclobutane and 1-methoxy-2, 2-dimethyl-3-methylenecyclobutane as simple methanol adducts of the starting bicy-clo[l.1.0]butane. In addition, 1:1:1 adducts of the starting bicyclo[1.1.0]butane, 1 -cyanonaphthalene, and methanol were isolated and characterized. Products were explained on the basis of a single electron transfer process from 1,2,2-trimethylbicyclo[1.1.0]butane to excited state 1-cyanonaphthalene to initially produce the cation radical of the bicyclo[1.1.0]butane and the anion radical of 1-cyanonaphthalene.