Phosphorus pentachloride → 2-(3,3,3-Trinitropropyl)-5-(perfluoropropyl)-1,3,4-oxadiazole
Reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N+:7]([C:10]([N+:32]([O-:34])=[O:33])([N+:29]([O-:31])=[O:30])[CH2:11][CH2:12][C:13]([NH:15][NH:16][C:17](=[O:28])[C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=O)([O-:9])=[O:8]>ClC(Cl)C>[N+:32]([C:10]([N+:7]([O-:9])=[O:8])([N+:29]([O-:31])=[O:30])[CH2:11][CH2:12][C:13]1[O:28][C:17]([C:18]([F:27])([F:26])[C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[N:16][N:15]=1)([O-:34])=[O:33]Participants
4
Procedure
Phosphorus pentachloride (1.2 g, 0.0057 mole) and N-(4,4,4-trinitrobutyryl)-N'-(perfluorobutyryl)hydrazine (0.8 g, 0.0018 mole) in 10mL of dichloroethane was held at reflux temperature for 4 hours. Removal of volatiles 9ave an oil which was washed with water and then chromatographed on Silica gel 40 (CH2Cl2 as eluent) to give 0.5 g (66%) of 2-(3,3,3-trinitropropyl)-5-(perfluoropropyl)-1,3,4-oxadiazole, mp 43°-45° C.; 1H NMR (acetone): 3.84 (m, 2H), 4.23 (m, 2H). Anal. Calcd for C8H4F7N5O7 : C, 23.14; H, 0.97; F, 32.04; N, 16.87. Found: C, 23.07; H, 1.00; F, 31.80; N, 16.95.