Deprotonation??Triggered Heavy??Halogen Migrations as a Key to the Structural Elaboration of 2, 2??Difluoro??1, 3??benzodioxole

J Gorecka, F Leroux, M Schlosser

Index: Gorecka, Joanna; Leroux, Frederick; Schlosser, Manfred European Journal of Organic Chemistry, 2004 , # 1 p. 64 - 68

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Citation Number: 3

Abstract

Abstract Although proton abstraction from the 4-position of 2, 2-difluoro-1, 3-benzodioxole occurs with exceptional ease, lithiation of the more-remote 5-position can only be brought about if no oxygen-adjacent site remains unoccupied. Thus, unlike 4-bromo-2, 2-difluoro-1, 3-benzodioxole (1),(7-bromo-2, 2-difluoro-1, 3-benzodioxol-4-yl) triethylsilane (5b) does react with lithium diisopropylamide to generate an intermediate that isomerizes ...