Homolytic Base-Promoted Aromatic Alkylations by Alkyl Halides1

…, GA Russell, WS Trahanovsky

Index: Wang, Chen; Russell, Glen A.; Trahanovsky, Walter S. Journal of Organic Chemistry, 1998 , vol. 63, # 26 p. 9956 - 9959

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Citation Number: 17

Abstract

Electron-transfer chain reactions leading to regioselective alkylations of benzenes bearing electron-withdrawing substituents can be observed with alkyl halides in the presence of the radical initiator (Bu3Sn) 2 and the proton acceptor 1, 4-diazabicyclo [2.2. 2] octane (DABCO). Yields vary from low to high depending on the benzene derivatives. The role of DABCO is to abstract a proton from the substituted cyclohexadienyl adduct radical to form ...