Issue 13, 2010
From the journal:

Chemical Communications

Structural elaboration of the surprising ortho-zincation of benzyl methyl ether†

Liam Balloch,a   Alan R. Kennedy,a   Jan Klett,a   Robert E. Mulvey*a  and  Charles T. O’Hara*a  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: r.e.mulvey@strath.ac.uk, charlie.ohara@strath.ac.uk

Abstract

Breaking with convention, the reaction of the sodium zincate, [(TMEDA)Na(μ-TMP)(μ-tBu)Zn(tBu)] with benzyl methyl ether (PhCH2OMe) produces exclusively an ortho-zincated intermediate [(TMEDA)Na(μ-TMP)(μ-C6H4CH2OMe)Zn(tBu)] instead of the expected “thermodynamic” α-metallated product.

Graphical abstract: Structural elaboration of the surprising ortho-zincation of benzyl methyl ether

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Article information

DOI
https://doi.org/10.1039/B924791B
Article type
Communication
Submitted
24 Nov 2009
Accepted
23 Dec 2009
First published
20 Jan 2010

Chem. Commun., 2010,46, 2319-2321

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Structural elaboration of the surprising ortho-zincation of benzyl methyl ether

L. Balloch, A. R. Kennedy, J. Klett, R. E. Mulvey and C. T. O’Hara, Chem. Commun., 2010, 46, 2319 DOI: 10.1039/B924791B

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