Synthesis of Novel Hexaazaisowurtzitane Cages to Access CL-20

被引：10

作者：

Aravindu, Pampuram ^{[1
]}

Rani, Karike Durga ^{[1
]}

Shaik, Abdul Munaf ^{[1
]}

Kommu, Nagarjuna ^{[1
]}

Rao, Vepa Kameswara ^{[1
]}

机构：

[1] Univ Hyderabad, Adv Ctr Res High Energy Mat, Hyderabad 500046, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 01期

关键词：

cage compounds; hexabenzylhexaazaisowurtzitane; hexacyclopropylhexaazaisowurtzitane; nitration; CL-20; STRAINED-RING COMPOUNDS; OPTIMIZATION; CONDENSATION; MECHANISM; GLYOXAL; CARBON; KEY;

D O I：

10.1002/ajoc.202100680

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel hexacyclopropylhexaazaisowurtzitane (HCPIW) and hexacyclobutylhexaazaisowurtzitane (HCBIW) cage compounds were synthesized using a straightforward method by reacting glyoxal with the corresponding cycloalkylamines such as cyclopropylamine and cyclobutylamine in the presence of a catalytic amount of an acid. The obtained compounds were characterized in detail by spectroscopic and X-ray diffraction analyses. HCPIW and HCBIW with 99% and 98% purity were obtained without column chromatography. Nitration of HCPIW with H2SO4/HNO3 in dichloromethane solvent successfully afforded CL-20, high energy propellant and explosive in 25% yield.

引用

页数：5

共 39 条

[1] Optimization of the Synthesis of 2,4,6,8,10,12-Hexaallyl-2,4,6,8,10,12-Hexaazaisowurtzitane
Adamiak, Joanna
Maksimowski, Pawel
[J]. PROPELLANTS EXPLOSIVES PYROTECHNICS, 2009, 34 (04) : 315 - 320
[2] [Anonymous], 1972, CHEM COMPANION
[3] CYCLIC AND LINEAR NITRAMINES FORMED BY NITROLYSIS OF HEXAMINE
BACHMANN, WE
HORTON, WJ
JENNER, EL
MACNAUGHTON, NW
SCOTT, LB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (06) : 2769 - 2773
[4] Advances in science and technology of modern energetic materials: An overview
Badgujar, D. M.
Talawar, M. B.
Asthana, S. N.
Mahulikar, P. P.
[J]. JOURNAL OF HAZARDOUS MATERIALS, 2008, 151 (2-3) : 289 - 305
[5] Balci M, 2000, ADV STR INT ORG MOL, V8, P43
[6] Impact of Stereo- and Regiochemistry on Energetic Materials
Barton, Lisa M.
Edwards, Jacob T.
Johnson, Eric C.
Bukowski, Eric J.
Sausa, Rosario C.
Byrd, Edward F. C.
Orlicki, Joshua A.
Sabatini, Jesse J.
Baran, Phil S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (32) : 12531 - 12535
[7] Optimization of Reductive Debenzylation of Hexabenzylhexaazaisowurtzitane (the Key Step for Synthesis of HNIW) Using Response Surface Methodology
Bayat, Yadollah
Ebrahimi, Heshmat
Fotouhi-Far, Farshad
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (11) : 1733 - 1738
[8] STUDIES OF THE SYNTHESIS, PROTONATION AND DECOMPOSITION OF 2,4,6,8,10,12-HEXABENZYL-2,4,6,8,10,12-HEXAAZATETRACYCLO[5.5.0.0(5,9).0(3,11)]DODECANE (HBIW)
CRAMPTON, MR
HAMID, J
MILLAR, R
FERGUSON, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (05): : 923 - 929
[9] An Improved and Scalable Synthesis of Insensitive High Explosive 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazaisowurtzitane (TEX)
Deshmukh, Mukesh B.
Borse, Amuirao U.
Mahulikar, Pramod P.
Dalal, Dipak S.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (07) : 1363 - 1369
[10] Condensation mechanism of cage hexabenzyl-hexaazaisowurtzitane from glyoxal and benzylamine: a computational study
Dong, Kai
Sun, Cheng-Hui
Zhang, Shao-Wen
Wang, Hui-Yun
Song, Jian-Wei
Pang, Si-Ping
[J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (21) : 12694 - 12699

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