Ozonolytic Decyclization of (R)-4-Menthen-3-one

Ozonolytic decyclization of (R)-4-menthen-3-one is accompanied by fragmentation of the isobutyl group, leading to -functionalized 3-methylpentanoic acid derivatives.     

Ozonolytic transformations of olefinic derivatives of L-menthol and ricinolic acid

Ozonolysis and reduction of olefinic derivatives of ricinolic acid and L-menthol were studied using hydroxylamine hydrochloride and sodium trisacetoxyborohydride to reduce the peroxide products. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 515–518, November–December, 2006.     

Novel synthesis of (4<Emphasis Type="Italic">R</Emphasis>)-4-methylpentanolide from (L)-(−)-menthol

A novel synthesis of the promising optically pure chiral (4R)-4-methylpentanolide that is based on several regiospecific oxidative transformations of (4R)-2,4-dimethyl-1-(1-methylethyl)-1-cyclohexene, the product of addition of (–)-menthone and methylmagnesium iodide followed by acid dehydration, was proposed.Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 451–453, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date.     

Transformations of peroxide olefin ozonolysis products under the action of hydroxylamine and semicarbazide hydrochlorides in isopropyl alcohol

Hydroxylamine and semicarbazide hydrochlorides were shown to be efficient as reducing agents toward peroxide products of ozonolysis of various olefins with different degrees of substitution. The rate of the transformations aldehyde → aldehyde oxime → nitrile → ester upon treatment of peroxides with hydroxylamine hydrochloride in isopropyl alcohol was lower than in methanol.     

Transformations of peroxide olefin ozonolysis products in methanol in the presence of water

Transformations of peroxide products of ozonolysis of various olefins with different degrees of substitution at the double bond by the action of hydroxylamine and semicarbazide hydrochloride in methanol in the presence of water as co-solvent were studied.     

Transformations of peroxide products of olefin ozonolysis under the action of semicarbazide in methanol

Peroxide products generated by ozonolysis of non-1-ene, 3-carene, stereoisomeric ??-pinenes, (?)-limonene, and castor oil were subjected to transformations by the action of semicarbazide and hydrazine-1,2-dicarboxamide in methanol.     

Synthesis and reactivity of metal-containing monomers. 20. Photochemical structurization of gelatin mixtures with the participation of transition metal acrylates

The structurization activity of cobalt, nickel, and copper acrylates in gelatin layers under the influence of monochromatic laser radiation with a wavelength of 633 nm has been studied. It has been established with the aid of IR and electronic spectroscopy that the complexation of the acrylate salts of Co(II), Ni(II), and Cu(II) with gelatin is accomplished by means of the OH groups of the hydroxyproline residues. It has been shown that the photosensitivity and density of the photographic layers are determined by the nature of the transition metal and increase along the series Co(II) < Ni(II) < Cu(II). Thin phase holograms with a diffraction efficiency () equal to 33% have been obtained.Institute of Chemical Physics, Russian Academy of Sciences, Chernogolovka 142432. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 576–581, March, 1992.     

Insect pheromones and their analogs. XLVII. Synthesis of 11-oxododeca-3,6-diynoic acid — The acyclic precursor of a macrolide component of pheromones of Oryzaephilus mercator and O. Surinamensis

A new approach is proposed to the synthesis of 11-oxododeca-3,6-diynoic acid — the acyclic precursor of a macrolide component of pheromones ofOryzaephilus mercator andO. surinamensis — from the readily available tetrahydropyran or allylacetone via the intermediate 5-bromo-2,2-ethylenedioxypentane.Institute of Organic Chemistry, Urals Division, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 288–292, March–April, 1993.     

A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid

A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination—dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu¹OK in the presence of dibenzo-18-crown-6 as the catalyst. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1637–1639, August, 1998.     

Insect pheromones and their analogues XL. Synthesis of dodec-3Z-EN-11RS-olide (ferrulactone II — A racemic analogue of a component of the aggregation pheromone of Cryptolestes ferrugineus

A new route, based on the partial ozonolysis of -acetyl derivatives of alk-1-en-4-ynes, is proposed for the synthesis of 11RS-hydroxydodec-3Z-enoic acid, the cyclization of which gives dodec-3Z-en-11RS-olide (ferrulactone II) — a racemic analogue of one of the macrolide components of the aggregation pheromone of the rust-red grain beetle.Institute of Organic Chemistry, Urals Branch, Russian Academy of Science,s Ufa. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 423–429, May–August, 1992.