Halogen-Metal Exchange in 1, 2-Dibromobenzene and the Possible Intermediacy of 1, 2-Dilithiobenzene

HF Bettinger, M Filthaus

Index: Bettinger, Holger F.; Filthaus, Matthias Journal of Organic Chemistry, 2007 , vol. 72, # 25 p. 9750 - 9752

Full Text: HTML

Citation Number: 21

Abstract

The one-step high-yield synthesis of 1, 2-bis (trimethylsilyl) benzene from 1, 2- dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1, 2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine-lithium exchange and subsequent derivatization reactions to ...