Preparation of Aliphatic gem-Dinitro Monoisocyanates and Derivatives

A Study of the 3,3,3‐Trinitropropyl Unit as a Potential Energetic Building Block

“…In this reaction, a diazonium salt is generated by in situ formed nitrous acid, which is subsequently displaced by a nucleophilic substitution with water. The urea derivative 4 is obtained by the reaction of two molecules of 1 by partial hydrolysis 6b. For the synthesis of bis(3,3,3‐trinitropropyl) oxalamide ( 5 ), the free amine generated from the hydrochloride salt 2 was reacted with oxalyl chloride 14.…”

Convenient synthesis of energetic polynitro materials including (NO2)3CCH2CH2NH3-saltsviaMichael addition of trinitromethane

“…The asymmetric (1). Selected atom distances (Å) and angles (°): C1-C2 1.502(2), C1-N1 1.540(2), C1-N2 1.538(2), C1-N3 1.521(1), C2-C3 1.524(2), C3-C4 1.522(2), C4-N4 1.332(2), C4-O7 1.237(1), N1-O1 1.211(1), N4-H5 0.89(2), N4-H6 −0.87(1), C2-C1-N2 114.15 (9), C2-C1-N1 112.09 (9), C2-C1-N3 110.49 (9), H6-N4-C4-C3 −178(1), H5-N4-C4-O7 −177(1), N4-C4-C3-C2 −157.3(1), C3-C2-C1-N1 −175.87 (9). (2).…”

Synthesis of novel polynitrodiols

“…However, no detailed description of the synthesis of either the alcohol or the acid chloride is given. In this work, the trinitropropanol was prepared via a trinitropropylamlne salt (6) by an adaptation of Eremenko's procedure for 3,3,3-fluorodlnitropropanol (7) or directly from 4,4,4-trinitrobutyric acid by a modified Schmidt reaction using triflic acid as the reaction medium. The conversion to 3,3-dinitropropanol and its acetate is straightforward.…”

“…After 1 h the mixture was acidified (H2S04), saturated with NaCI, and extracted with ether. The extract was dried (MgS04) and freed from solvent to give 15.0 g (82%) of crude dlol as a pale yellow oil: 1H NMR (CDCI3) 7.29 (t), 6.60 (t), 3.15 (m), 2.55 (broad m).…”

“…A crude liquid product (2.8 g) that remained after removal of volatiles in vacuo provided 1.32 g (42%) of crystals (mp 76-80 °C) from dichloromethane/ hexane. An analytical sample was obtained by further recrystallization, with mp 84-85 °C: 1H NMR (CDCI3) 5.18 (d of t, 1, JCh2-ch = 4 Hz, JCH.CF = 18 Hz), 4.91 1-Fluoro-1,1,6,6-tetranltro-4-oxa-2,7-heptanedlol (6).…”