Stereoelectronic effects in the deprotonation of arylalkyl radical cations: meso-ethylanthracenes

…, AE Popp, L Gelbaum, LA Bottomley

Index: Tolbert, Laren M.; Khanna, Rajive K.; Popp, Ann E.; Gelbaum, Leslie; Bottomley, Lawrence A. Journal of the American Chemical Society, 1990 , vol. 112, # 6 p. 2373 - 2378

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Citation Number: 57

Abstract

Abstract: In contrast to meso-methylanthracenes, which are oxidized by one-electron oxidants to hydroxymethyl derivatives, meso-ethylanthracenes such as 9, lO- diethylanthracene (DEA) undergo a facile chemical or biochemical oxidative elimination of ethylene to yield an anthrone. No trace of ethyl side chain oxidation to a I-hydroxyethyl derivative is observed. The rationale for this dramatic selection between methyl and ethyl ...