Reactions of tert-butyllithium with. alpha.,. omega.-dihaloalkanes. Evidence for single-electron-transfer-mediated metal-halogen interchange involving alkyl radical- …

WF Bailey, RP Gagnier, JJ Patricia

Index: Bailey, William F.; Gagnier, Paul R.; Patricia, Jeffrey J. Journal of Organic Chemistry, 1984 , vol. 49, # 12 p. 2098 - 2107

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Citation Number: 58

Abstract

The reactions of tert-butyllithium (t-BuLi) with primary a-iodo-w-haloalkanes and a, o- dibromoalkanes have been investigated in experiments conducted at-23 OC in n-pentane- diethyl ether (3: 2 by volume) solution. It has been found that production of an a-lithio-w- haloalkane (1) by metal-halogen interchange at one end of a 1, 3-, 1, 4-, or 1, 5-dihalide results in intramolecular coupling to give cycloalkanes in high yield. As the chain length of ...