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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 15, 1985 - Issue 6
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Original Articles

Synthesis of 8Z, 10z-Dodecadienyl Acetate Using a General Method Applicable to Z,Z-1,3-Dienes

Fredrik Björkling Department of Organic Chemistry, Royal Institute of Technology, S-100 44, STOCKHOLM, Sweden
,
Torbjörn Norin Department of Organic Chemistry, Royal Institute of Technology, S-100 44, STOCKHOLM, Sweden
&
Rikard Unelius Department of Organic Chemistry, Royal Institute of Technology, S-100 44, STOCKHOLM, Sweden
Pages 463-472 | Published online: 06 Dec 2006
 
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Abstract

Coupling of 9Z-iodo-1-(2-tetrahydropyranyloxy)-8-non-ene (6) and 1Z-propenylzinc (9) in the presence of Pd(PPH3)4 gave 1-(2-tetrahydropyranyloxy)-8Z,10Z-dodecadiene (10) in 90% yield. Deprotection, crystallisation and acetylation then gave a yield of 65% (from 4) of the title compound which was > 99% pure.

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