The Abnormal Behavior of an Atropisomer: 3, 3′??Dibromo??1, 1′??difluoro??2, 2′??binaphthyl Reacting with Alkyllithium Compounds

…, G Mangano, M Schlosser

Index: Leroux, Frederic; Mangano, Giuseppe; Schlosser, Manfred European Journal of Organic Chemistry, 2005 , # 23 p. 5049 - 5054

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Citation Number: 3

Abstract

Abstract 1-Fluoro-2-(triethylsilyl) naphthalene (1) and other 1-fluoronaphthalenes bearing a metalation-resistant substituent at the 2-position proved to be totally inert toward base attack. 3-Bromo-1-fluoronaphthalene (6), readily prepared from the 2-bromo isomer 5 by deprotonation-triggered heavy halogen migration, was converted into 3, 3′-dibromo-1, 1′- difluoro-2, 2′-binaphthyl (8) by consecutive treatment with lithium diisopropylamide, ...