Tetrahedron

Competition of substituents for ortho direction of metalation of veratric acid

…, TH Nguyen, AS Castanet, KPP Nguyen, J Mortier

Index: Chau, Nguyet Trang Thanh; Nguyen, Thi Huu; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques Tetrahedron, 2008 , vol. 64, # 46 p. 10552 - 10557

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Citation Number: 13

Abstract

LTMP (5equiv) metalates randomly veratric acid (1). Under external quench conditions, the thermodynamically more stable lithium 2-lithio-3, 4-dimethoxybenzoate (2) reacts with a variety of electrophiles to give versatile building units that are not easily accessible by conventional means. Under in situ quench conditions (LTMP/TMSCl), a reversal of regioselectivity is observed and 6-trimethylsilyl-3, 4-dimethoxybenzoic acid (10) is formed ...

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