Abstract
Pyrolysis of dibenzyl ether (DBE) in tetralin-d 12 allowed discrimination between possible free radical and concerted reaction mechanisms. Pyrolysis product spectra contained both α-deuteriotoluene and perprotiotoluene, relative fractions of which were determined, by complementary 1H and 13C n.m.r. analyses, to vary with the initial ratio of tetralin-di 12 to DBE. Mathematical extrapolation to DBE pyrolysis at infinite dilution indicated that its thermolysis in tetralin-d 12 was entirely via free radical mechanisms.
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