Attempts To Trap Radicals Formed in Solution by a Magnesium Surface

Article abstract of DOI:10.1021/jo00049a026

The synthesis of 2,2'-azo-2-methyl-6-heptene (1) is discribed.Photolytic decomposition of 1 in ether gave rise to the 1,1-dimethyl-5-hexenyl radical clock (2) which yielded 1,1,2-trimethylcyclopentane (3), 6-methyl-1-heptene (4), and 2-methyl-1,6-heptadiene (5) in the ratio of 1:0.72:0.56, respectively.The ratio did not change appreciably when a well-stirred mixture of 1 and 5 equiv of magnesium powder was photolyzed.Moreover, the solution gave a negative test (2,2'-biquinoline) for the presence of Grignard reagent.Thus, it has been esperimentally demonstrated that the radicals formed in solution do not react with a magnesium surface to form Grignard reagents.