Abstract
AbstractThe thermolysis of tetramethyl‐1,2‐dioxetane (1) in degassed 1,4‐cyclohexadiene affords products attributable to hydrogen abstraction from solvent by excited acetone: benzene + 2‐propanol (.14–.15 moles each per mole 1), 1,4‐dihydrocumyl alcohol (2‐[2,5‐cyclohexadien‐1‐yl]‐2‐propanol) (.05 moles per mole 1), and a small amount of tetrahydrobiphenyls. These products are formed in the same proportions during the irradiation of acetone in degassed 1,4‐cyclohexadiene. The rate and kinetic order of the decomposition of 1 is the same as in air‐saturated solvents, where no acetone reduction products are observed. Comparison of the product yields with the known rate of quenching of acetone triplets by cyclohexadiene leads to the conclusion that at least one‐third of the quenching is of the nonreactive type, accompanying capture of allylic hydrogen from the hydrocarbon. The mechanism of the reaction is discussed, and a comparison is drawn between different radicals and anions in their modes of coupling with the cyclohexadienyl radical.
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