Issue 4, 2000
From the journal:

Chemical Communications

Facile β-trimethylstannyl promoted 1,5-hydride shifts in cyclooctyl and cyclodecyl systems

Matthew P. Glenn,a   Kerry G. Penmana  and  William Kitching*a  

* Corresponding authors

a Department of Chemistry, The University of Queensland, Brisbane, Queensland, Australia.
E-mail: kitching@chemistry.uq.edu.au

Abstract

Deuterium labelling and 2H NMR mapping demonstrate that cyclooctyl and cyclodecyl mesylates in aqueous EtOH exhibit greatly enhanced or exclusive levels of 1,5-hydride shift, provided a Me3Sn group is β to the migrating hydrogen, and after tin group loss from the formal β-stannyl cation, results in regiospecific, transannular alkene formation.

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Article information

DOI
https://doi.org/10.1039/A909463F
Article type
Communication
Submitted
30 Nov 1999
Accepted
19 Jan 2000
First published
10 Feb 2000

Chem. Commun., 2000, 309-310

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Facile β-trimethylstannyl promoted 1,5-hydride shifts in cyclooctyl and cyclodecyl systems

M. P. Glenn, K. G. Penman and W. Kitching, Chem. Commun., 2000, 309 DOI: 10.1039/A909463F

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