95926-83-3Relevant academic research and scientific papers
Sterically Hindered Free Radicals, XII. The Radical tert-Butyldiphenylmethyl, Its Dimer, and Their Autoxidation. A Reinvestigation
Zarkadis, Antonios K.,Neumann, Wilhelm P.,Marx, Rainer,Uzick, Wolfram
, p. 450 - 456 (2007/10/02)
The radical Ph2C.-tBu (1) dimerizes giving reversibly the quinonoid derivative 3, and not the ethane-like 2 as reported in the literature.In equilibrium there are less radicals 1 than in the case of triphenylmethyl, ΔHdiss = 18.5 +/- 2 kcal/mol for 3.Both the radical 1 and its dimer 3 are rapidly oxidized by oxygen. 1 gives the dialkyl peroxide 6 which fragmentates already at 20 deg C mainly to benzophenone and tBu., 3 leads to the ketone 7, probably via the hydroperoxide 10. 3 rearranges catalysed by acid and by base as well via a 1,5-hydrogen migration forming the benzenoid derivative 4.Preparative and ESR details are given.
