128540-78-3Relevant academic research and scientific papers
SIMPLE SYNTHESIS OF ACETOGENIN TRANSOID INSECT PHEROMONES STARTING FROM ACETYLCYCLOPROPANE
Cheskis, B. A.,Ivanova, N. M.,Moiseenkov, A. M.,Nefedov, O. M.
, p. 1372 - 1380 (1991)
A highly effective synthesis of a series of alkyl and 1-alkenyl cyclopropyl ketones, which are key components in the complete synthesis of a large number of transoid lepidoptera pheromones, has been developed, based on the alkylation of N-cyclohexyl-1-cyclopropylethylideneimine or its condensation with aldehydes.
Generation and intermolecular capture of cyclopropylacyl radicals
Heinrich, Markus R.,Zard, Samir Z.
, p. 4969 - 4972 (2007/10/03)
(Chemical Equation Presented) Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced β-elimination of the xanthate group.
Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones
Moiseenkov, Alexander M.,Czeskis, Boris A.,Ivanova, Natalya M.,Nefedov, Oleg M.
, p. 2639 - 2649 (2007/10/02)
Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.
SIMPLE SYNTHESIS OF &β-SILYLOXYACYLCYCLOPROPANES AND THE HOMOALLYL REARRANGEMENT OF CYCLOPROPYLCARBINOLS BY THE ACTION OF TRIMETHYLSILYL HALIDES IN THE PRESENCE OF ZINC HALIDES
Cheskis, B. A.,Ivanova, N. M.,Moiseenkov, A. M.,Nefedov, O. M.
, p. 1839 - 1849 (2007/10/02)
The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave β-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones.Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides.The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.
