Catalytic        2,3,4-hexatriene formation by terminal alkyne coupling at calcium

Anthony G. M. Barrett; Mark R. Crimmin; Michael S. Hill; Peter B. Hitchcock; Sarah L. Lomas; Panayiotis A. Procopiou; Kogularamanan Suntharalingam

doi:10.1039/B818848C

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Catalytic 2,3,4-hexatriene formation by terminal alkyne coupling at calcium†

Anthony G. M. Barrett,*^a Mark R. Crimmin,^a Michael S. Hill,*^b Peter B. Hitchcock,^c Sarah L. Lomas,^b Panayiotis A. Procopiou^d and Kogularamanan Suntharalingam^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Imperial College London, Exhibition Road, South Kensington, London, UK

^b Department of Chemistry, University of Bath, Claverton Down, Bath, UK
E-mail: msh27@bath.ac.uk

^c The Chemistry Laboratory, University of Sussex, Falmer, Brighton, UK

^d GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, UK

Abstract

Heteroleptic calcium amides effect the catalytic dimerisation of the terminal alkyne CH₃OCH₂C [triple bond, length as m-dash] CH to the hexatriene (CH₃OCH₂)CH [double bond, length as m-dash] CCCH(CH₂OCH₃) under mild conditions; the reaction is proposed to occur via a dimeric calcium acetylide intermediate and to be promoted by polarisation of the electron density within the alkynide C [triple bond, length as m-dash] C bonds.

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Article information

DOI: https://doi.org/10.1039/B818848C
Article type: Communication
Submitted: 24 Oct 2008
Accepted: 04 Mar 2009
First published: 27 Mar 2009

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Chem. Commun., 2009, 2299-2301

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Catalytic 2,3,4-hexatriene formation by terminal alkyne coupling at calcium

A. G. M. Barrett, M. R. Crimmin, M. S. Hill, P. B. Hitchcock, S. L. Lomas, P. A. Procopiou and K. Suntharalingam, Chem. Commun., 2009, 2299 DOI: 10.1039/B818848C

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