The reductive O,C-coupling of halopentafluoroacetones

Translated from Izvestiya Akademii Nauk SSSR. Seriya Khimicheskaya, No. 9, pp. 2142–2144, September, 1989.     

Synthesis of 3,3,4,4-tetrafluoro-4-iodobutylamine,a bifunctional reagent for ionic and free-radical reactions

1,1,2,2-Tetrafluoro-1,4-diiodobutane reacts with NaN3 under phase-transfer catalysis conditions to give 3,3,4,4-tetrafluoro-4-iodobutyl azide. The reduction of the azide with triphe-nylphosphine followed by hydrolysis of intermediate iminophosphorane affords 3,3,4,4-tetra-fluoro-4-iodobutylamine.     

Synthesis, E/Z-isomerization, and cycloaddition of (E)- and (Z)-4,4,4-trifluoro-2-butenenitrile to anthracene

4,4,4-Trifluoro-2-butenenitrile was synthesized by the Wittig reaction of trifluoroacetaldehyde and cyanomethylidenetriphenylphosphorane and separated to individual E- and Z-isomers by rectification. Each isomer undergoes stereospecific [4+2] cycloaddition to anthracene.     

Synthesis of 2-trichloromethyloxazolidin-5-ones by reaction of chloral with N,O-trimethylsilyl derivatives of amino acids

The corresponding 2-trichloromethyloxazolidin-5-ones were obtained by reaction of chloral with trimethylsilyl (TMS) derivatives of some amino acids. The corresponding oxazolidin-5-ones could not be obtained by the action of chloral on aspartic and glutamic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1472–1473, November, 1978.     

Thermal and BF<Subscript>3</Subscript>⋅Et<Subscript>2</Subscript>O-catalyzed cleavage of 1-hydrohexafluoroisobutenyloxytrimethylsilane. Perfluoromethacrolein,its isomers,dimers, and homopolymers

During vacuum pyrolysis in a quartz or steel tube, 1-hydrohexafluoroisobutenyloxytrimethylsilane (1) eliminates fluorotrimethylsilane to give perfluoromethacrolein, which was detected by NMR. Similar pyrolysis of silane 1 over KF results in E- and Z--hydrotetrafluoromethacryloyl fluorides. At 20 °C, perfluoromethacrolein undergoes homopolymerisation and/or cyclodimerization to yield 4,4-difluoro-2-pentafluoroisopropenyl-5-trifluoromethyl-4H-1,3-dioxin, which rearranges into E-7,7,7-trifluoro-2,6-bis(trifluoromethyl)-4-oxahepta-2,5-dienoyl fluoride under the action of BF₃Et₂O. The same fluoride is also formed, together with fluorotrimethylsilane, directly from silane 1 under the action of BF₃Et₂O.Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1629–1635, August, 2004.Deceased     

E,Z-Isomers of 3-ethoxy-4,4,4-trifluorobut-2-enenitrile and N-methylpyrrolidines derived from them

Russian Chemical Bulletin - 3-Ethoxy-4,4,4-trifluorobut-2-enenitrile was synthesized by the Wittig reaction of ethyl trifluoroacetate and (cyanomethylidene)triphenylphosphorane and was separated to...