Synthesis of Biisoxazoletetrakis(methyl nitrate): A Potential Nitrate Plasticizer and Highly Explosive Material

作者: Leah A. Wingard , Eric C. Johnson , Pablo E. Guzmán , Jesse J. Sabatini , Gregory W. Drake

DOI: 10.1002/EJOC.201700280

关键词:

摘要: The efficient and scalable synthesis of 3,3′-biisoxazole-4,4′,5,5′-tetrakis(methyl nitrate) its energetic properties are described. features a metal-free [3+2] cycloaddition an electron-rich internal alkyne nitrile oxide by simple heating, without using halogenated solvents. material has favorable sensitivity properties, point toward potential as nitrate plasticizer highly explosive material.

参考文章(18)
T. P. Kofman, A. E. Trubitsin, I. V. Dmitrienko, E. Yu. Glazkova, Synthesis and properties of 5-substituted 1-dinitromethyl-3-nitro-1 H-1,2,4-triazoles Russian Journal of Organic Chemistry. ,vol. 44, pp. 874- 881 ,(2008) , 10.1134/S1070428008060171
Byoung Sun Min, Young Chul Park, A study on the aliphatic energetic plasticizers containing nitrate ester and nitramine Journal of Industrial and Engineering Chemistry. ,vol. 15, pp. 595- 601 ,(2009) , 10.1016/J.JIEC.2009.01.017
A. S. Ermakov, E. Yu. Petrov, D. B. Vinogradov, Fam Van Toai, A. P. Denisyuk, D. L. Rusin, New plasticizers for energetic materials Theoretical Foundations of Chemical Engineering. ,vol. 41, pp. 660- 667 ,(2007) , 10.1134/S0040579507050351
Neville Marsh, Alexander Marsh, A Short History Of Nitroglycerine And Nitric Oxide In Pharmacology And Physiology Clinical and Experimental Pharmacology and Physiology. ,vol. 27, pp. 313- 319 ,(2000) , 10.1046/J.1440-1681.2000.03240.X
Betsy M. Rice, Jennifer J. Hare, Edward F. C. Byrd, Accurate predictions of crystal densities using quantum mechanical molecular volumes. Journal of Physical Chemistry A. ,vol. 111, pp. 10874- 10879 ,(2007) , 10.1021/JP073117J
Edward F. C. Byrd, Betsy M. Rice, A Comparison of Methods To Predict Solid Phase Heats of Formation of Molecular Energetic Salts Journal of Physical Chemistry A. ,vol. 113, pp. 345- 352 ,(2009) , 10.1021/JP807822E
Scott Grecian, Valery V. Fokin, Ruthenium-Catalyzed Cycloaddition of Nitrile Oxides and Alkynes: Practical Synthesis of Isoxazoles† Angewandte Chemie. ,vol. 47, pp. 8285- 8287 ,(2008) , 10.1002/ANIE.200801920
Pasupala Ravi, Dilip M. Badgujar, Girish M. Gore, Surya P. Tewari, Arun K. Sikder, Review on Melt Cast Explosives Propellants, Explosives, Pyrotechnics. ,vol. 36, pp. 393- 403 ,(2011) , 10.1002/PREP.201100047
Yinglei Wang, Kangzhen Xu, Fengqi Zhao, Yueping Ji, Jianhua Yi, Siyu Xu, Fulei Gao, Bin Chen, Synthesis, Crystal Structure, and Thermal Behaviors of 3-Nitro-1,5-bis(4,4′-dimethylazide)-1,2,3-triazolyl-3-azapentane (NDTAP) Propellants, Explosives, Pyrotechnics. ,vol. 38, pp. 644- 650 ,(2013) , 10.1002/PREP.201200146
I. V. Tselinskii, V. V. Tolstyakov, S. M. Putis, S. F. Mel’nikova, Synthesis and study of thermal stability of 3-nitro-1,2,4-triazole N-nitroxy-and N-azidomethyl derivatives Russian Chemical Bulletin. ,vol. 58, pp. 2356- 2361 ,(2009) , 10.1007/S11172-009-0327-5