Ortho methyl group effects in cumyl systems

JW Timberlake, D Pan, J Murray…

Index: Timberlake, Jack W.; Pan, Dawei; Murray, Jane; Jursic, Branko S.; Chen, Tonghua Journal of Organic Chemistry, 1995 , vol. 60, # 16 p. 5295 - 5298

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Citation Number: 10

Abstract

In an attempt to evaluate the steric effect of ortho methyl groups on the stability of the cumyl radical, 2, 2', 4, 4', 6, 6'-hexamethylazocumene (6) was synthesized and its rate of decomposition was measured. The fact that 6 decomposes 40 times faster than azocumene is attributed to a ground state steric effect. Calculations on the mesitylcumyl radical 1 and cation 2 show both systems to be substantially nonplanar with dihedral angles of 48" and ...