Sandmeyer reactions. Part 5. 1 Estimation of the rates of 1, 5-aryl/aryl radical translocation and cyclisation during Pschorr fluorenone synthesis with a comparative …

SA Chandler, P Hanson, AB Taylor…

Index: Chandler, Stephen A. Journal of the Chemical Society, Perkin Transactions 2, 2001 , # 2 p. 214 - 228

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Citation Number: 2

Abstract

During the Pschorr cyclisation of 2-aroylphenyl radicals, a rearrangement occurs reversibly by 1,5-hydrogen transfer to give 2-benzoylaryl radicals. Rate constants of (1.2 ± 0.2) × 10 6 s −1 at 293 K are estimated for both the forward and back reactions in the equilibrium between 2-(4-methylbenzoyl)phenyl and 2-benzoyl-5-methylphenyl radicals. Assuming an empirical estimate of 1.6 × 10 −2 dm 3 mol −1 s −1 for the hypothetical rate of abstraction of hydrogen from ...