Aggregative activation in heterocyclic chemistry. Part 4. Metallation of 2-methoxypyridine: unusual behaviour of the new unimetal superbase BuLi–Me 2 N (CH 2) 2 …

P Gros, Y Fort, P Caubère

Index: Gros, Philippe; Fort, Yves; Caubere, Paul Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 20 p. 3071 - 3080

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Citation Number: 67

Abstract

A series of potential unimetal superbases BuLi–ROLi has been studied in order to increase the basicity/nucleophilicity ratio ([B/N] R) of BuLi. The best [B/N] R ratio is found with BuLi– LiDMAE. This complex base apparently metallates 2-methoxypyridine at the unexpected C-6 position. It is shown that no actual metallated species are formed in the reaction medium, the reaction occurring as the result of a common radical precursor stabilized by an aggregate ...