Aggregative activation in heterocyclic chemistry .4. Metallation of 2-methoxypyridine: unusual behaviour of the new unimetal superbase BuLi-Me2N(CH2)(2)OLi (BuLi-LiDMAE)

被引：60

作者：

Gros, P ^{[1
]}

Fort, Y ^{[1
]}

Caubere, P ^{[1
]}

机构：

[1] UNIV NANCY 1,FAC SCI,LAB CHIM ORGAN 1,CNRS,URA 457,F-54506 VANDOEUVRE NANCY,FRANCE

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 20期

关键词：

D O I：

10.1039/a701914i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 Cd 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 cluster. Finally, as an application, Ca substituted 2-methoxypyridines have been obtained in good to excellent yields.

引用

页码：3071 / 3080

页数：10

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