Synthesis of bis-(2-fluoro-2, 2-dinitroethyl) nitramine and tris-(2-fluoro-2,2-dinitroethyl) amine

Gafurov, R. G.; Свиридов, С. И.; Natsibullin, F. Ya.; Erëmenko, L. T.

doi:10.1007/bf00853379

Cited by 1 publication

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“…The various nitrogen bases, diethylamine, ethylamine (70% in water), dimethylamine (25% in water), methylamine (40% in (10) It is readily calculated from the dissociation constant of isopropylamine (Kb = 4.27 X 10"4 at 25 °C; cf. pKB, Table I), for example, that an 0.82 M aqueous solution delivering 2 molar equiv of the amine with respect to TNBzCl, as employed in this study, initially provides only about 0.04 molar equiv of OH".…”

Section: Kb Amine + H20mentioning

confidence: 99%

Conversion of 2,4,6-trinitrobenzyl chloride to 2,2',4,4',6,6'-hexanitrostilbene by nitrogen bases

Sollott¹

1982

J. Org. Chem.

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trifluoroacetate. An axial/equatorial preference of 5:95 was achieved. Experimental SectionGeneral Methods. Reactions were conducted under argon in a 25-mL two-necked flask fitted with a rubber septum. Liquids were transferred via argon-flushed syringes. Benzene and toluene were distilled from sodium/benzophenone ketyl; tris(triphenylphosphine)rhodium(I) chloride and tris(tripenylphosphine)ruthenium(II) dichloride were obtained from Alfa, Danvers, MA; alkylsilanes were obtained from Petrarch Systems, Bristol PA, and used without purification. An authentic mixture of cis-and trans-4-tert-butylcyclohexanol for GLC comparison was prepared by lithium aluminum hydride reduction of 4-tert-butylcyclohexanone in ether.11 Triethylsilyl deuteride12 and 2,2,6,6-tetradeuterio-4-tert-butylcyclohexanone13 were prepared by literature methods.GLC analyses were obtained on a Perkin-Elmer 3920 gas chromatograph fitted with a flame-ionization detector. Separations were provided by a 6 ft X V8 in., 5% 2:1 FFAP/Bentone aluminum column.Triethylsilane/Rhodium(I)-Catalyzed Reduction. To an orange homogeneous solution of 154 mg (1.00 mmol) of 4-tertbutylcyclohexanone and 45 mg (0.050 mmol) of tris(triphenylphosphine)rhodium(I) chloride in 5.0 mL of benzene was added 0.24 mL (1.5 mmol) of triethylsilane. The reaction mixture turned yellow and was heated at reflux for 1 h. The resulting deep red solution was concentrated by rotary evaporation. The residual oil was diluted with 5 mL of hexane, filtered, concentrated, and chromatographed on silica gel (3% ether-hexane) to afford 249 mg (92%) of c¿s,trons-[(4-tert-butylcyclohexyl)oxy]triethylsilane as a colorless liquid: IR (film)

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Section: Kb Amine + H20mentioning

confidence: 99%

Conversion of 2,4,6-trinitrobenzyl chloride to 2,2',4,4',6,6'-hexanitrostilbene by nitrogen bases

Sollott¹

1982

J. Org. Chem.

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show abstract

Synthesis of bis-(2-fluoro-2, 2-dinitroethyl) nitramine and tris-(2-fluoro-2,2-dinitroethyl) amine

Cited by 1 publication

References 3 publications

Conversion of 2,4,6-trinitrobenzyl chloride to 2,2',4,4',6,6'-hexanitrostilbene by nitrogen bases

Conversion of 2,4,6-trinitrobenzyl chloride to 2,2',4,4',6,6'-hexanitrostilbene by nitrogen bases

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