Journal of the American Chemical Society p. 6683 - 6689 (1994)
Update date:2022-08-16
Topics:
Tanner, Dennis D.
Zhang, Liying
The solution-phase reactions of microwave-generated hydrogen atoms with terminal olefins is regioselective. Since addition is to the terminal end of the olefin, the reaction yields a secondary radical which undergoes either reaction with molecular or atomic hydrogen, disproportionation, combination, or addition to another olefin, and in the case of hydrogen atom addition to 1,6-heptadiene, cyclization. The cyclized radicals are formed reversibly, and the final product mixture contains only minor amounts of cis-1,2-dimethylcyclopentane (the product of kinetic control) while the major cyclized product is methylcyclohexane. Although an equilibrium mixture could not be obtained, the dimethylcyclopentyl and 3-methylcyclohexyl radicals were shown to be formed reversibly.
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