Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism

T Cohen, H Gibney, R Ivanov, EAH Yeh…

Index: Cohen, Theodore; Gibney, Heather; Ivanov, Roman; Yeh, Edmund A.-H.; Marek, Ilan; Curran, Dennis P. Journal of the American Chemical Society, 2007 , vol. 129, # 49 p. 15405 - 15409

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Citation Number: 32

Abstract

The cyclizations of a number of terminally unsaturated alkenyl zinc iodides to cyclopentylmethylzinc iodides, formerly believed to be nonradical in nature, have been revealed as radical chain cyclizations initiated by adventitious oxygen. Five cases are presented in which the published carbozincation cis/trans selectivities are essentially the same as those found for the cyclizations of the unsaturated alkyl iodide precursors of the ...