Synthesis of a fluorinated analog of the sex pheromone of the processionary moth thaumetopoea. pityocampa(denis and schiff.) |
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| Institution: | 1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, 15 Beisanhuan East Road, Chaoyang District, Beijing 100029, PR China;2. State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, 15 Beisanhuan East Road, Chaoyang District, Beijing 100029, PR China;1. School of Environment, Resources and Sustainability, University of Waterloo, 200 University Avenue West, Waterloo N2L 3G1, ON, Canada;2. Graduate Department of Forestry, University of Toronto, 33 Willcocks St, Toronto, Ontario M5S 3B3, Canada;3. Department of Biology and the Vale Living with Lakes Centre, Laurentian University, 935 Ramsey Lake Road, Sudbury P3E 2C6 ON, Canada;1. Egyptian Petroleum Research Institute, 1-Ahmed El-Zomr St., P.O. Box 11727, Nasr City, Cairo, Egypt;2. Leibniz-Institut für Katalyse, Rostock, Germany |
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| Abstract: | The synthesis of ()-13-fluorohexadec-13-en-11-ynyl acetate , a fluorinated analog of the sex pheromone of the processionary moth Thaumetopoea pityocampa is described. The synthetic scheme involves epoxidation of the double bond, regioselective opening of the oxirane ring with Olah's reagent, tosylation of the resulting fluorohydrin and dehydrotosylation. Structural features of the intermediate diastereomeric fluorohydrins and and tosylates and are also discussed on the basis of their 1H and 19F NMR spectra. |
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