- SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
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Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
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Paragraph 0258
(2018/09/12)
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- Biologically active compounds by catalytic olefin metathesis
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Biologically active compounds such as pheromones and precursors thereof are produced by catalyzed cross metathesis of dissimilar terminal olefins or of a cyclodiene and a terminal olefin.
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- STADIES ON THE WITTIG REACTION (VIII). STEREOSELECTIVITY OF DIPHENYL ALLYLIC PHOSPHONIUM YLIDS IN WITTIG REACTION
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Ylids generated from diphenyl allylic phosphonium salts reacted with aliphatic aldehydes containing a terminal oxygen functionized group in the absence of lithium salt to give E,E-conjugated dienes.The stereoselectivity depends mainly on the base used, the allylic part of phosphonium salts also shows some effect on stereochemistry.Eight conjugated dienic insect sex pheromones and related analogues with different E-selectivities were obtained.
- Wenfang, Huang,Jun, Zhu,Wenjing, Xiao,Yanneng, Deng
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- Mass Spectra of Dodecadienic Compounds with a Conjugated Double Bond, Lepidopterous Sex Pheromones
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All geometrical isomers of 5,7-, 6,8-, 7,9-, 8,10- and 9,11-dodecadien-1-ols, and their acetates and aldehyde derivatives were analyzed by electron impact mass spectrometry.The abundance of molecular ion (M(1+)) was observed in every spectrum, and the relative intensity of M(1+) tended to be strong if the compound possessed an (E)-double bond(s).In addition to M(1+), (1+) (alcohols) and (1+) (acetates), every dienic compound showed typical series of CnH(2n-2)(1+)CnH(2n-5)(1+) with abundance maxima around C4, C5, C6 or C7.Each double bond positional isomer characteristically yielded different ion peaks in the series, which were useful for its distinction from other isomers.These results indicate that the chemical structure of a natural pheromone of Lepidoptera is easily deduced successfully by GC-MS analysis if it is a conjugated dienic pheromone.
- Ando, Tetsu,Katagiri, Yoshio,Uchiyama, Masaaki
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p. 413 - 422
(2007/10/02)
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- Ethylaluminum Dichloride Catalyzed Ene Reactions of Aldehydes with Nonnucleophilic Alkenes
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Ethylaluminum dichloride, which is a strong Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic aldehydes with nonnucleophilic alkenes.Higher aldehydes give good yields of ene adducts with terminal alkenes.Formaldehyde gives good yields of adducts with electron-deficient alkenes.This reaction has been used for the synthesis of recifeiolide, ricinelaidic acid, and the insect pheromones (E,E)-8,10-dodecadienyl acetate and (E)-9,11-dodecadienyl acetate.
- Snider, Barry B,Phillips, Gary B.
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p. 464 - 469
(2007/10/02)
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- Simple, Stereospecific Syntheses of Some Insect Pheromones using the -Fe(CO)3 Protecting Group
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(Diene)Fe(CO)3 complexes have been used for totally stereospecific syntheses of insect pheromones having (E)- and (E,E)-1,3-diene skeletons.
- Knox, Graham R.,Thom, Ian G.
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p. 373 - 374
(2007/10/02)
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