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

Anjum Ahmed*, Jonathan Clayden, Michael Rowley

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

52 Citations (Scopus)

Abstract

Deuterium labelling shows that an intramolecular proton transfer ('anion translocation') is a key step in the mechanism leading to an α-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 α-lithiation, though for undeuterated amides a parallel mechanism also operates in which lithiation occurs directly at the position α to nitrogen.

Original languageEnglish
Pages (from-to)6103-6106
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number34
DOIs
Publication statusPublished - 20 Aug 1998

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