The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure

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

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

The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure

Abstract:

New and practical synthesis of (E)-11-tetradecen-1-yl acetate and (Z)-11-hexadecen-1-yl acetate were developed. The synthesis were based on a C12+C2=C14 and C12+C4=C16 coupling scheme. 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 was effected by adding 1-tert-butoxy-10-bromodecane to monosodate acetylene, obtained in situ from DMSO and sodium hydride. It was prepared 1-tert-butoxy-dodec-11-yne, which is transformed in di[tert-butoxy-dodec-11-yne]mercury, the common intermediate in the synthesis of the two pheromones. In order to obtain (E)-11-tetradecen-1-yl acetate, the mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-tetradec-11-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-tetradec-11-yne and acetylation gave (E)-11-tetradecen-1-yl acetate with 99 % isomeric purity. In order to obtain (Z)-11-hexadecen-1-yl acetate, the mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-hexadec-11-yne. After acetylation of 1-tert-butoxy-hexadec-11-yne and stereoselective reduction in the presence of NiP-2 catalyst gave (Z)-11-hexadecen-1-yl acetate with 90 % isomeric purity.

Keywords:
(E)-11-tetradecen-1-yl acetate; (Z)-11-hexadecen-1-yl acetate; Lepidoptera; sex pherome

Issue: 2018, Volume 69, Issue 6

Pages: 1315-1318

Publication date: 2018/7/15

https://doi.org/10.37358/RC.18.6.6317

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
ANDREICA, A.M., GANSCA, L., CIOTLAUS, I., OPREAN, I., The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure, Rev. Chim., 69(6), 2018, 1315-1318.

Vancouver
Andreica AM, Gansca L, Ciotlaus I, Oprean I. The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure. Rev. Chim.[internet]. 2018 Jun;69(6):1315-1318. Available from: https://doi.org/10.37358/RC.18.6.6317

APA 6th edition
Andreica, A.M., Gansca, L., Ciotlaus, I. & Oprean, I. (2018). The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure. Revista de Chimie, 69(6), 1315-1318. https://doi.org/10.37358/RC.18.6.6317

Harvard
Andreica, A.M., Gansca, L., Ciotlaus, I., Oprean, I. (2018). 'The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure', Revista de Chimie, 69(6), pp. 1315-1318. https://doi.org/10.37358/RC.18.6.6317

IEEE
A.M. Andreica, L. Gansca, I. Ciotlaus, I. Oprean, "The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure". Revista de Chimie, vol. 69, no. 6, pp. 1315-1318, 2018. [online]. https://doi.org/10.37358/RC.18.6.6317

Text
Adriana Maria Andreica, Lucia Gansca, Irina Ciotlaus, Ioan Oprean,
The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure,
Revista de Chimie,
Volume 69, Issue 6,
2018,
Pages 1315-1318,
ISSN 2668-8212,
https://doi.org/10.37358/RC.18.6.6317.
(https://revistadechimie.ro/Articles.asp?ID=6317)
Keywords: (E)-11-tetradecen-1-yl acetate; (Z)-11-hexadecen-1-yl acetate; Lepidoptera; sex pherome

RIS
TY - JOUR
T1 - The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure
A1 - Andreica, Adriana Maria
A2 - Gansca, Lucia
A3 - Ciotlaus, Irina
A4 - Oprean, Ioan
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2018
VL - 69
IS - 6
SP - 1315
EP - 1318
UR - https://doi.org/10.37358/RC.18.6.6317
KW - (E)-11-tetradecen-1-yl acetate
KW - (Z)-11-hexadecen-1-yl acetate
KW - Lepidoptera
KW - sex pherome
ER -

BibTex
@article{RevCh2018P1315,
author = {Andreica Adriana Maria and Gansca Lucia and Ciotlaus Irina and Oprean Ioan},
title = {The Use of Mercury Compounds in the Synthesis of Some Lepidoptera Insect Sex Pheromones with Monoenic Structure},
journal = {Revista de Chimie},
volume = {69},
number = {6},
pages = {1315-1318},
year = {2018},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.18.6.6317},
url = {https://revistadechimie.ro/Articles.asp?ID=6317}
}

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