Substituent Effects on Oxidation??Induced Formation of Quinone Methides from Arylboronic Ester Precursors

S Cao, R Christiansen, X Peng

Index: Cao, Sheng; Christiansen, Robin; Peng, Xiaohua Chemistry - A European Journal, 2013 , vol. 19, # 27 p. 9050 - 9058

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Citation Number: 18

Abstract

Abstract A series of arylboronic esters containing different aromatic substituents and various benzylic leaving groups (Br or N+ Me 3 Br−) have been synthesized. The substituent effects on their reactivity with H 2 O 2 and formation of quinone methide (QM) have been investigated. NMR spectroscopy and ethyl vinyl ether (EVE) trapping experiments were used to determine the reaction mechanism and QM formation, respectively. QMs were not ...