61529-79-1Relevant academic research and scientific papers
The Ambident Reactivity of Triphenylmethyl Radicals in Hydrogen-abstraction Reactions and the Mechanism of the Base-catalysed Rearrangement of (Diphenylmethylene)cyclohexadienes (a Type of Semibenzene) into Triphenylmethane
Huszthy, Peter,Lempert, Karoly,Simig, Gyula,Tamas, Jozsef,Hegedus-Vajda, Judit,Toth, Gabor
, p. 491 - 498 (2007/10/02)
Thermolysis of tri(phenyl)(phenylazo)methane (2) in non-deuteriated 2,2-dimethoxypropane in the presence of non-deuteriated sodium methoxide furnishes, among other products, mixtures of the deuteriated analogues of triphenylmethane (1c) and of deuteriated analogues of (p-biphenylyl)diphenylmethane (3a).The former was shown to be a mixture of the hexadecadeuterio derivative (6c) and the isomeric monoprotiopentadecadeuterio derivatives (6a and b), while the latter proved to be a mixture of the pentaprotio derivative (3d) and the isomeric hexaprotio derivatives (3b and c).The formation of compound (6b) proves the ambident reactivity of triphenylmethyl radicals in hydrogen-abstraction reactions, while the observed ratio of compounds (6a and b) indicates the rearrangements of the intermediate semibenzenes (7) and (8) to be multistep conducted-tour rearrangements (Scheme 1).
