Hydrogen Abstraction by Benzyl Radicals

Abstract

DIBENZYLMERCURY (I) decomposes readily on heating at 170° or above to form mercury and dibenzyl^1–3. 9,10-Dihydroanthracene (II) is a hydrogen transfer reagent which has been used in several reactions where a hydrogen donor is required, for example, the formation of quinols from quinones⁴ and the hydrogenation of thiyl radicals to form thiols⁵. When (I) was thermally decomposed under nitrogen in the presence of (II) at 210°–215° the products obtained were mercury, dibenzyl, toluene and 9,9′, 10,10′-tetrahydrodianthranyl-9,9′ (III), m.p. 249°, which was identified by combustion analysis (calc. for C₂₈H₂₂ : C, 93.85; H, 6.15; found: C, 93.9; H, 6.1), mixed meltingpoint with an authentic sample (mixed m.p. 249°) and conversion to 9,10-dibromoanthracene by reaction with bromine in carbon disulphide⁶.