Chlorine → HCID 20162005, compound

HRID 247234Notes

Reaction equation

HRID 247234 reaction equation
ClCl.[N+:3]([C:6]([N+:23]([O-:25])=[O:24])([CH2:9][O:10][CH2:11][O:12][CH2:13][C:14]([N+:20]([O-:22])=[O:21])([N+:17]([O-:19])=[O:18])[CH2:15][OH:16])[CH2:7][OH:8])([O-:5])=[O:4].ClC(SS[C:32]([O:53][CH2:54][C:55]([F:62])([N+:59]([O-:61])=[O:60])[N+:56]([O-:58])=[O:57])([O:43][CH2:44][C:45]([N+:50]([O-:52])=[O:51])([N+:47]([O-:49])=[O:48])[F:46])[O:33][CH2:34][C:35]([N+:40]([O-:42])=[O:41])([N+:37]([O-:39])=[O:38])[F:36])(Cl)Cl>ClCCCl>[F:36][C:35]([N+:37]([O-:39])=[O:38])([N+:40]([O-:42])=[O:41])[CH2:34][O:33][C:32]([O:53][CH2:54][C:55]([N+:56]([O-:58])=[O:57])([N+:59]([O-:61])=[O:60])[F:62])([O:43][CH2:44][C:45]([N+:47]([O-:49])=[O:48])([N+:50]([O-:52])=[O:51])[F:46])[O:16][CH2:15][C:14]([N+:17]([O-:19])=[O:18])([N+:20]([O-:22])=[O:21])[CH2:13][O:12][CH2:11][O:10][CH2:9][C:6]([N+:23]([O-:25])=[O:24])([N+:3]([O-:5])=[O:4])[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 24526ChlorineHCID 131492082-{Bis(2-fluoro-2,2-dinitroethoxy)[(trichloromethyl)disulfanyl]methoxy}-1-fluoro-1,1-dinitroethaneHCID 158075003,3'-[Methylenebis(oxy)]bis(2,2-dinitropropan-1-ol)

Product 1

HCID 20162005HCID 20162005, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

Chlorine gas was passed into a solution of 3.78 g (0.011 mol) of 2,2,8,8-tetranitro-4,6-dioxanonane-1,9-diol and 6.53 g (0.01 mol) of tris(2-fluoro-2,2-dinitroethoxy)methyl trichloromethyl disulfide in 20 ml of dry 1,2-dichloroethane at 65° C. for two hours. Heating at 65° C. was continued for 22 hours at which time the solvent was removed and the oily residue was washed with 2×30 ml of hexane. Thin layer chromatography indicated the product was a mixture of the mono-(XI) and the bis-orthocarbonate (XII). The mono-orthocarbonate (XI) was isolated by column chromatography (silica gel 60, methylene chloride-ethyl acetate (90:10) as eluent) as a viscous gummy oil; H-NMR [(CD3)2C=O]: δ 5.20 (d), 4.96 (s), 4.83 (s), 4.68 (s), 4.58 (s), 4.54 (s). IR (film on NaCl plate) 3600 (OH), 1600 (NO2) cm-1.

Workup

  1. customthe solvent was removed
  2. washthe oily residue was washed with 2×30 ml of hexane
  3. additiona mixture of the mono-(XI)

Sources & evidence

ORD record
ord-8ac92bd2d6c940b186f69659c9aad246
Source dataset
uspto-grants-1987_11
Patent number
US04705899

Reaction notes

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