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

Vitaly Raev; Peter G. Jones; Henning Hopf

doi:10.1055/s-0032-1316901

Synlett, Table of Contents

Synlett 2013; 24(8): 995-997
DOI: 10.1055/s-0032-1316901

letter

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

Authors

Vitaly Raev

^aInstitute 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

^bInstitute 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*

^aInstitute of Organic Chemistry, Technical University of Braunschweig, Hagenring 30, 38106 Braunschweig, Germany Fax: +49(531)3915288 Email: h.hopf@tu-bs.de

Abstract

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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

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References

References and Notes
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