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Revista de Chimie (Rev. Chim.), Year 2017, Volume 68, Issue 1, 157-162

https://doi.org/10.37358/RC.17.1.5410

Irina Ciotlaus, Lucia Gansca, Adriana Maria Andreica, Ioan Oprean

A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones

Abstract:

New and practical synthesis of (Z)-8-dodecene-1-yl acetate and (E)-8-dodecene-1-yl acetate were developed. The synthesis were based on a C3+C6=C9 and C9+C3=C12 coupling scheme, the starting material being 2-propyn-1-ol and 1,6-hexandiol. The routes involve, as the key step, the use of the same mercury derivative of the terminal-alkyne w-functionalised as intermediate. The first coupling reaction took place between methoxyallene and Grignard reagent of 1-tert-butoxy-6-bromo-hexan obtaining 1-tert-butoxy-non-8-yne, which is transformed in di<1-tert-butoxy-non-8-yne>mercury, the common intermediate in the synthesis of the two pheromones. In order to obtain (Z)-8-dodecene-1-yl acetate and (E)-8-dodecene-1-yl acetate, the mercury derivative was directly lithiated and then alkylated with 1-bromo-propan obtaining 1-tert-butoxy-dodec-8-yne. After acetylation of 1-tert-butoxy-dodec-8-yne and stereoselective reduction in the presence of NiP-2 catalyst gave (Z)-8-dodecene-1-yl acetate with 85 % isomeric purity. After reduction with lithium aluminium hydride of 1-tert-butoxy-dodec-8-yne and acetylation was obtained (E)-8-dodecene-1-yl acetate with 90% isomeric purity.
Keywords:
(Z)-8-dodecene-1-yl acetate; (E)-8-dodecene-1-yl acetate; Lepidoptera; sex pheromone

Issue: 2017, Volume 68, Issue 1
Pages: 157-162
Publication date: 15/02/2017
https://doi.org/10.37358/RC.17.1.5410
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Creative Commons License
This article is published under the Creative Commons Attribution 4.0 International License
Citation Styles
Cite this article as:
CIOTLAUS, I., GANSCA, L., ANDREICA, A.M., OPREAN, I., A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones, Rev. Chim., 68(1), 2017, 157-162.

Vancouver
Ciotlaus I, Gansca L, Andreica AM, Oprean I. A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones. Rev. Chim.[internet]. 2017 Jan;68(1):157-162. Available from: https://doi.org/10.37358/RC.17.1.5410


APA 6th edition
Ciotlaus, I., Gansca, L., Andreica, A.M. & Oprean, I. (2017). A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones. Revista de Chimie, 68(1), 157-162. https://doi.org/10.37358/RC.17.1.5410


Harvard
Ciotlaus, I., Gansca, L., Andreica, A.M., Oprean, I. (2017). 'A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones', Revista de Chimie, 68(1), pp. 157-162. https://doi.org/10.37358/RC.17.1.5410


IEEE
I. Ciotlaus, L. Gansca, A.M. Andreica, I. Oprean, "A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones". Revista de Chimie, vol. 68, no. 1, pp. 157-162, 2017. [online]. https://doi.org/10.37358/RC.17.1.5410


Text
Irina Ciotlaus, Lucia Gansca, Adriana Maria Andreica, Ioan Oprean,
A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones,
Revista de Chimie,
Volume 68, Issue 1,
2017,
Pages 157-162,
ISSN 2668-8212,
https://doi.org/10.37358/RC.17.1.5410.
(https://revistadechimie.ro/Articles.asp?ID=5410)
Keywords: (Z)-8-dodecene-1-yl acetate; (E)-8-dodecene-1-yl acetate; Lepidoptera; sex pheromone


RIS
TY - JOUR
T1 - A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones
A1 - Ciotlaus, Irina
A2 - Gansca, Lucia
A3 - Andreica, Adriana Maria
A4 - Oprean, Ioan
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2017
VL - 68
IS - 1
SP - 157
EP - 162
UR - https://doi.org/10.37358/RC.17.1.5410
KW - (Z)-8-dodecene-1-yl acetate
KW - (E)-8-dodecene-1-yl acetate
KW - Lepidoptera
KW - sex pheromone
ER -


BibTex
@article{RevCh2017P157,
author = {Ciotlaus Irina and Gansca Lucia and Andreica Adriana Maria and Oprean Ioan},
title = {A Practical Synthesis of (Z)- and (E)-8-Dodecene-1-yl Acetate, Components of Lepidoptera Insect Sex Pheromones},
journal = {Revista de Chimie},
volume = {68},
number = {1},
pages = {157-162},
year = {2017},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.17.1.5410},
url = {https://revistadechimie.ro/Articles.asp?ID=5410}
}
 
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