Synthesis of α,α,ι,ι-Tetranitroalkanes¹

Chemistry of the Aliphatic Polynitro Compounds and Their Derivatives

“…The synthesis of gem-dinitro compounds from 1nitro-l-haloalkanes by the displacement of halogen with nitrite ion in basic media is well known. Recent examples include the preparation of the potassium salt of dinitromethane (29), 2,2-dinitroethanol from 2-bromo-2-nitroethanol (66), and 1,1,4,4tetranitrobutane from l,4-dibromo-l,4-dinitrobutane (31). The general applicability of the ter Meer reaction to higher a,«-dibromo-a,w-dinitroalkanes has not been studied for two reasons:…”

Cyanoethylation. I. Weakly Basic Catalysts in the Reaction of Acrylonitrile with Active Methylene Compounds1

“…downfield from tetramethylsilane as internal standard) of 2.64 («-protons), 1.39 (ß-and 7-protons), and 1.14 (N-protons); intensity ratios 4:4:1. For comparison, the spectrum of redistilled piperidine was determined at a similar concentration; the chemical shifts (14) The X-ray patterns were kindly obtained by Dr.'Arthur L. Draper and Mr. Richard L. Garner using a Phillips X-ray diffraction unit with Cr Ka radiation. We desire to express our gratitude for these, determinations.…”

Synthesis of Energetic Monomers and Polymers

“…Also, literature reports on substituent effects on ring-opening polymerization indicate that bulky substituents often favor ring over open chain structures. In order to test these effects in the case of nitrodiols, 2,2,5,5-tetranitrohexanediol 15 was reacted with CH20/H2SO4. The product was essentially completely insoluble in CH 2 Cl 2 which rules out the presence of the 9-membered ring formal 11.…”