Insect pheromones and their analogues XXIV. Synthesis of long-chain 1,5-dimethyl-branched pheromones from geranyl acetate

Schemes for the synthesis of long-chain 1,5-dimethyl-branched pheromones (7,11-dimethyloctadecane, 15,19-dimethyltritriacontane, and 2-acetoxy-3,7-dimethylpentadecane) from the product of the allyl oxidation of geranyl acetate (8-acetoxy-2,6-dimethylocta-2E,6E-dien-1-ol) have been developed.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 818–823, November–December, 1990.     

Insect pheromones and their analogs. VII. Synthesis of the sex pheromone of the fruit flyCeratitis capitata

A new and simple route to the synthesis of non-6E-en-l-ol (I) — the pheromone of the fruit flyCeratitis capitata Wiedemann — has been proposed on the basis of the readily available co-oligomer of butadiene and phenol, 1-phenoxyocta-2E, 7-diene (II).     

Synthesis of 13,13,14,14,15,15,16,16-octafluoro-11E,Z-hexadecen-1-yl acetate

A synthesis was reported for 13,13,14,14,15,15,16,16-octafluoro-11-hexadecen-1-yl acetate, which is an analog of the sex pheromone of the cabbage worm(Mamestra Brassicae).Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2165–2167, September, 1990.     

Mass spectra of negative ions of aliphatic ω-oxocarboxylic acid derivatives

Conclusions Fragmentation of the molecules of methyl esters of aliphatic -oxocarboxylic acids upon dissociative capture of electrons includes processes of fragmentation that are characteristic for each functional group individually. It has been established that terminal functional groups separated by a saturated chain of four carbon atoms will interact, thus demonstrating that this molecule can exist in the folded conformation.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2238–2246, October, 1984.     

Ozonolysis of Alkenes and Studies of Reactions of Polyfunctional Compounds: LXV. Ozonolysis of Perfluoro-1-octene in Freon-113

Ozonization of perfluoro-1-octene in Freon-113 yields the corresponding ozonide whose catalytic hydrogenation over Pd/C or hydride reduction leads to formation of perfluoroheptanoic acid; the reduction with lithium aluminum hydride gives 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-heptanol. Ozonization of perfluoro-1-octene in Freon-113 containing excess (3 equiv) alcohol affords the corresponding perfluoroheptanoic acid ester.     

Identification and Biological Activity of Volatile Organic Compounds Isolated from Plants and Insects. III. Chromatography-Mass Spectrometry of Volatile Compounds of Aegopodium podagraria

Gas chromatography-mass spectrometry identified more than 20 volatile organic compounds isolated from leaves and flowers ofAegopodium podagrariaL.     

The first synthesis of spirocyclopentyl derivatives of lupane triterpenoids by radical nitrocyclization of C-2-diallyl substituted betulonates

Radical cyclization of the 1,6-hexadiene moiety in 2,2-diallyl substituted methyl or benzyl dihydrobetulonates initiated by Fe(NO₃)₃·9H₂O in the presence of FeCl₃ or LiCl gave hitherto unknown spirocyclic compounds in which ring A of the lupane triterpenoid at position C-2 is spiro coupled with a vicinally substituted nitromethyl- and chloromethylcyclopentane. Based on a quantum-chemical assessment of the energy characteristics of this reaction, the most probable configurations of the chiral atoms in the spirocyclopentane ring were determined for the major diastereomers isolated in individual form.