Anion translocation in organolithiums: A mechanism for the lithiation and cyclisation of tertiary naphthamides

被引：54

作者：

Ahmed, A

Clayden, J

Rowley, M

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

[2] Merck Sharp & Dohme Ltd, Neurosci Res Ctr, Harlow CM20 2QR, Essex, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 34期

关键词：

D O I：

10.1016/S0040-4039(98)01291-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deuterium labelling shows that an intramolecular proton transfer ("anion translocation") is a key step in the mechanism leading to an alpha-lithiated tertiary naphthamide and thence to the products of anionic cyclisation. The kinetic isotope effect means that proton transfer from the ortho position can become the sole mechanism for alpha-lithiation, though for undeuterated amides a parallel mechanism also operates in which lithiation occurs directly at the position alpha to nitrogen. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6103 / 6106

页数：4

共 24 条

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