Syntheses of pure (9Z, 11Z), (9E, 11E), (9E, 11Z), and (9Z,11E)-9,11-hexadecadienals-possible candidate pheromones |
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Authors: | P. I. Svirskaya S. N. Maiti A. J. Jones B. Khouw C. C. Leznoff |
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Affiliation: | (1) Department of Chemistry, York University, M3J IP3 Downsview, Ontario, Canada;(2) The National NMR Centre, Australian National University, 2600 Canberra, ACT, Australia |
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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. |
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Keywords: | (9z,11Z) (9E.11E) (9E,11Z) (9Z,11E)-9 11-Hexadecadienals (9E)-hexadecen-11-yn-1-yl acetate syntheses aldehydes ester conjugated dienes dienals |
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