Synthesis of 7E,9Z-dodecadienyl acetate,the sex pheromone ofLobesia botrana Shiff |
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| Authors: | Z G Chrelashvili M V Mavrov A V Dolidze A P Voronkov E P Serebryakov |
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| Institution: | (1) P. G. Melikishvili Institute of Physical and Organic Chemistry, Georgian Academy of Sciences, 380086 Tbilisi, Georgia;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(3) State Research and Designing Institute of the Methanol Industry (GOSNIIMETANOLPROEKT), 344940 Severodonetsk, Ukraine |
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| Abstract: | Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates. The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy- -chlorohydrins) as alkylating agents.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 766–768, April, 1993. |
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| Keywords: | 7E 9Z-dodecadienyl acetate synthesis organocuprates cross-coupling 2E 4Z-heptadienyl acetate 1-bromo-3E 5Z-octadiene 1 3-butadiyne |
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