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Synlett 2013; 24(8): 995-997
DOI: 10.1055/s-0032-1316901
letter
© Georg Thieme Verlag Stuttgart · New York

Zirconium-Induced Cyclizations of Long-Chain α,ω-Diyne Derivatives – The Surprising One-Pot Formation of Dimeric Structures

Vitaly Raev
a   Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, 38106 Braunschweig, Germany   Fax: +49(531)3915288   Email: h.hopf@tu-bs.de
,
Peter G. Jones
b   Institute of Inorganic and Analytical Chemistry, Technical University of Braunschweig, Hagenring 30, 38106 Braunschweig, Germany   Fax: +49(531)3915387   Email: p.jones@tu-bs.de
,
Henning Hopf*
a   Institute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, 38106 Braunschweig, Germany   Fax: +49(531)3915288   Email: h.hopf@tu-bs.de
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Further Information

Publication History

Received: 08 February 2013

Accepted after revision: 18 March 2013

Publication Date:
10 April 2013 (online)

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Abstract

Dimeric products were produced besides the monomeric (and expected) cyclization product, on subjecting diacetylenes to the conditions developed by Negishi (ZrCp2 from ZrCp2Cl2 and ­BuLi). The structures of the dimeric products were established by spectroscopic data and single-crystal X-ray structural analysis. The mechanisms leading to their formation are discussed.

Key words

Zr-promoted cyclizations - macrocyclic rings - cyclopentadienones - bicyclo[5.3.0]decanes - transition-metal catalysis
 

  • References and Notes

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