Related Experiment Video
Updated: Feb 22, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Dinitromethyl-3(5)-1,2,4-oxadiazole Derivatives from Controllable Cyclization Strategies
Yongxing Tang1, Chunlin He1, Gregory H Imler2
1Department of Chemistry, University of Idaho, Moscow, Idaho, 83844-2343, USA.
Abstract:
N-Cyanoimidate (1) with hydroxylamine hydrochloride in the presence of triethylamine gives different products (2 a or 2 b) as a function of the sequence of reactant addition. Further oxidation/nitration/decarboxylation/acidification reactions of 2 a/2 b generate dinitromethyl-3(5)-1,2,4-oxadiazole derivatives, including a surprising energetic compound with high oxygen balance, 3-(dinitromethyl)-1,2,4-oxadiazol-5-one (5) as well as 5,5'-dinitromethyl-3,3'-azo-1,2,4-oxadiazole (9). Some salts of 5 and 9 as precursors were also prepared. All were fully characterized using multinuclear NMR and IR spectroscopy, and elemental analyses as well as low-temperature single-crystal X-ray diffraction for 4, 5, 7 and 8. In addition, their properties (thermal stability, detonation performance and sensitivity to impact and friction) were investigated. Among them, 5 and 8 show promising detonation performance as energetic materials.
More Related Videos
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
10:42Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Cycloaddition Reactions: Overview
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry