Pheromones of coleoptera. Communication 3. Synthesis of R-γ-hexanolide from D-mannitol

Conclusions R--Hexanolide, a component of the sex pheromone of the beetleTrogoderma glabrum, was produced from D-mannitol in seven steps with a total yield of 3–3.5%.For communication 2, see [1].Translated from Izvestiya Akademii Nauk SSSR,- Seriya Khimicheskaya, No. 11, pp. 2605–2606, November, 1985.     

Pheromones of coleoptera. Communication 5. Synthesis of R,E-14-methyl-8-hexadecenal (trans-trogodermal)

Conclusions A short synthesis of R,E-14-methyl-8-hexadecenal (trans-trogodermal) from 1,1-ethylene-dioxy-8-acetoxy-9-decene and R-(-)-1-bromo-4-methylhexane was realized.Translated from Izvestiya Akademii Nauk SSSR, Seriya, Khimicheskaya, No. 4, pp. 903–906, April, 1987.     

Pheromones of coleoptera. Communication 6. Synthesis of R,Z-14-methyl-8-hexadecenal (cis-trogodermal)

Conclusions The simple synthesis of optically active R,Z-14-methyl-8-hexadecenal (cis-trogodermal), the principal components of the aggregation pheromone ofTrogoderma granarium, was accomplished. The synthesis was based on the use of R-1-bromo-4-methylhexane and Z-4-chloro-2-buten-1-ol as the sources of the chiral and olefin fragments.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 906–910, April, 1987.     

Attractant pheromones of coleoptera. Communication 1. Simple synthesis of exo- and endo-brevicomins using the oxy-cope rearrangement

Conclusions A five-stage synthesis of exo- and endo-brevicomins was carried out from acrolein and methyl vinyl ketone, with an oxy-Cope rearrangement of 4-ethyl-3-methyl-1,5-hexadien-3-ol as the key stage.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1887–1890, August, 1985.     

Attractant pheromones of coleoptera. Communication 2. Simple synthesis of (±)-frontalin using low-temperature oxy-cope rearrangement

Conclusions An effective four-stage synthetis of (±)-frontalin from mesityl oxide has been developed with a low-temperature oxy-Cope rearrangement as the key stage.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1890–1892, August, 1985.     

Differential thermal analysis of polyethylene under high pressure

The design of a differential thermal analysis apparatus for use at elevated pressure is described. Experiments on melting and crystallization of folded-chain crystals of polyethylene and poly(ethylene–butene-1) copolymer, and melting of extended-chain polyethylene crystals have been conducted at pressures up to 4200 bars. The precision in transition temperature measurement was ±1°C. The Clausius-Clapeyron equation predicts the melting point increase with pressure at atmospheric pressure to be 32.0°C/kb. The melting point depression due to copolymerization remained constant over the complete pressure range analyzed on the poly(ethylene–butene-1) used in this study. Crystallization of polyethylene is retarded at elevated pressures, and a 50% larger degree of supercooling is necessary at 5000 bars to give a crystallization rate equal to that observed at atmospheric pressure. The difference in melting point between folded-chain and extended-chain polyethylene increases from 8.4°C at 1 bar to 25.6°C at 3000 bars.     

Synthesis of 5-ketotetrazoles under high pressure

Conclusions The reaction of -ketonitriles with hydrazoic acid and organic azides at high pressure is an effective method for the synthesis of 5-acyltetrazoles.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1168–1170, May, 1988.     

Synthesis of titanium sulfides under high pressure

Titanium sulfides were synthesized in the temperature range 600–750°C and in the pressure range 10–200 MPa with an apparatus used for hydrothermal synthesis. Stoichiometric TiS₂ cannot be prepared under atmospheric pressure, but was synthesized under high pressure. Also the phase relationship between TiS₂ and TiS₃ has been established under high pressure up to 200 MPa, and the pressure-temperature phase diagram for TiS system is presented.     

Synthesis of polyisocyanurates by thermal rearrangement of polycyanurates

Polyisocyanurates have been successfully prepared by the thermal rearrangement of polycyanurates, which were obtained from 2,4‐dichloro‐6‐methoxy‐1,3,5‐triazine and bisphenol monomers. The thermal rearrangement was carried out in the presence of a small amount of tetrabutylammonium bromide (TBAB) as a catalyst at 200 °C for 30 or 60 min in an argon atmosphere, and the degree of arrangement was greater than 95%. Transparent and amorphous polyisocyanurate films were obtained and showed a good thermal stability with a 5% weight loss temperature above 340 °C in nitrogen and the glass transition temperature above 210 °C. Films with a 10‐µm thickness exhibited an excellent transparency above 90% at 400 nm. Furthermore, the thermal rearrangement of 2,6‐bis(4‐methoxyphenyl)‐6‐methoxy‐1,3,5‐triazine to 1,3‐bis(4‐methoxyphenyl)‐5‐methyl‐1,3,5‐triazinane‐2,4,6‐trione was investigated in detail. It was found that the complete thermal rearrangement was successfully accomplished in the presence of 2 wt % TBAB at 150 °C for 20 min in an argon atmosphere. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015 , 53, 692–698     

Synthesis of pyridines from 1,2,4-triazines under high pressure

A procedure has been proposed for the synthesis of pyridines from 1,2,4-triazine derivatives and bicyclo[2.2.1]hepta-2,5-diene under high pressure in the presence of lithium perchlorate as catalyst.     

Coleopteran pheromones. Communication 10. Synthesis of the chiral pheromone of the eleven-spotted leaf beetle (coleoptera: Chrysamelidae)

Conclusions The synthesis of (R)-10-methyl-2-tridecanone from the chiral (S)-3,7-dimethyl-1,6-octadiene was accomplished with the total yield of 24–26% in the 13–14 stages of the synthesis.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2083–2085, September, 1987.It corresponds to Communication 5 in the series Terpenes in Organic Synthesis. For the preceding Communication 9, cf. [1].     

Synthesis of high molecular weight polystyrene using AGET ATRP under high pressure

High molecular weight polystyrene (PS) was synthesized by ATRP. Under atmospheric pressure (1 bar), PS with M_n up to 200,000 was prepared using either ARGET or ICAR ATRP. Under high pressure (6 kbar), higher molecular weight PS could be obtained due to accelerated radical propagation and diminished radical termination in polymerization of styrene. Therefore, it was possible to synthesize PS with M_n > 1,000,000 and M_w/M_n < 1.25 using AGET ATRP under a pressure of 6 kbar at room temperature. This is the highest molecular weight linear PS prepared by a controlled radical polymerization.     

Effect of high pressure on rearrangement of organosilicon peroxides

Conclusions The thermal rearrangement of organosilicon peroxides to alkoxysiloxanes proceeds with a substantial decrease in the volume activation effect.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 484–485, February, 1978.