Syntheses of pure (9Z, 11Z), (9E, 11E), (9E, 11Z), and (9Z,11E)-9,11-hexadecadienals-possible candidate pheromones
- 1 May 1984
- journal article
- research article
- Published by Springer Nature in Journal of Chemical Ecology
- Vol. 10 (5) , 795-807
- https://doi.org/10.1007/bf00988544
Abstract
The title compounds were prepared by six different routes, and recommendations are given for the more convenient procedures in laboratory-scale syntheses. Modifications in the literature preparations of the 9E,11E and 9E,11Z isomers are described. Baseline separation of a prepared mixture of all four isomers of the (9Z, 11Z), (9E, 11E), (9E, 11Z), and (9Z, 11E)-9,11-hexadecadienals was achieved using GC methods with standard capillary columns. [13C]NMR spectroscopy of the alkene carbon atoms clearly differentiates between theZ,Z, E,E and eitherE,Z orZ,E isomers of the precursor dienols and thus of the dienals.Keywords
This publication has 21 references indexed in Scilit:
- Synthesis of (Z,Z)-11,13-hexadecadienal, a principal component of navel orangeworm (Pamyelois transitella) pheromoneThe Journal of Organic Chemistry, 1983
- Synthesis of sex pheromone components of the forest tent caterpillar,Malacosoma disstria (Hübner) and of the western tent caterpillar,Malacosoma californicum (Packard)Journal of Chemical Ecology, 1981
- Isolation, identification, and synthesis of a female sex pheromone of the navel orangeworm,Amyelois transitella (Lepidoptera: Pyralidae)Journal of Chemical Ecology, 1979
- 13C NMR of some insect attractants and related compoundsTetrahedron, 1978
- Hydroboration. 45. New, convenient preparations of representative borane reagents utilizing borane-methyl sulfideThe Journal of Organic Chemistry, 1977
- The synthesis of insect sex phermonesTetrahedron, 1977
- Fatty acids. Part 50. 13C nuclear magnetic resonance studies of olefinic fatty acids and estersChemistry and Physics of Lipids, 1977
- Reaktionen mit Phosphinalkylenen, XXXIII. Darstellung lithiumsalzfreier Ylidlösungen mit Natrium‐bis(trimethylsilyl)amid als BaseEuropean Journal of Inorganic Chemistry, 1976
- Stereoselective synthesis of alkyl (2E,4E)- and (2Z,4E)-3,7,11-trimethyl-2,4-dodecadienoates. Insect growth regulators with juvenile hormone activityThe Journal of Organic Chemistry, 1975
- Carbon-13 Fourier transform nuclear magnetic resonance. VIII. Role of steric and electric field effects in fatty acid spectraThe Journal of Organic Chemistry, 1974