Nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo[ 5.5.3.02,6.04,10.08,12] pentadecane

Cheng Hui Sun; Xin Qi Zhao

Nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo[ 5.5.3.0^2,6.0^4,10.0^8,12] pentadecane

Cheng Hui Sun^*, Xin Qi Zhao

^*Corresponding author for this work

School of Material Science and Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

In order to develop a new energetic materials, nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3 ,5 ,7 ,9,11-hexaazapentacyclo [5.5. 3. 0^2,6. 0^4,10. 0^8,12] pentadecane (I) was studied in detail. I was nitrolyzed selectively to 4-nitratomethyl-2,6, 8, 12-tetraacetyl-10-nitro-2,4,6,8,10,12-hexaazaisowurtzitane (II) with HNO₃/Ac₂O. While with mixture of nitric and sulfuric acids as nitration reagent, at 80 °C directly or at 15 °C 2 h firstly then 80 °C I was nitrolyzed to CL-20 or 4-nitratomethyl-2,6,8,10,12-pentanitrohezaazaisowurtzitane (III) respectively. II can also be nitrated to HI. The structures of two new hexaazaisowurtzitane derivatives (II and I) were confirmed by MS,IR,¹H NMR and ¹³C NMR.

Original language	English
Pages (from-to)	1-3
Number of pages	3
Journal	Hanneng Cailiao/Chinese Journal of Energetic Materials
Volume	17
Issue number	1
Publication status	Published - Feb 2009

Keywords

3,5,9, 11-tetraacetyl-14-oxo-1, 3, 5, 7, 9, 11-hexaazapentacyclo [5.5.3.0.0.0] pentadecane
Hexaazaisowurtzitane derivative
Organic chemistry
Selective nitration

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title = "Nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo[ 5.5.3.02,6.04,10.08,12] pentadecane",

abstract = "In order to develop a new energetic materials, nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3 ,5 ,7 ,9,11-hexaazapentacyclo [5.5. 3. 02,6. 04,10. 08,12] pentadecane (I) was studied in detail. I was nitrolyzed selectively to 4-nitratomethyl-2,6, 8, 12-tetraacetyl-10-nitro-2,4,6,8,10,12-hexaazaisowurtzitane (II) with HNO3/Ac2O. While with mixture of nitric and sulfuric acids as nitration reagent, at 80 °C directly or at 15 °C 2 h firstly then 80 °C I was nitrolyzed to CL-20 or 4-nitratomethyl-2,6,8,10,12-pentanitrohezaazaisowurtzitane (III) respectively. II can also be nitrated to HI. The structures of two new hexaazaisowurtzitane derivatives (II and I) were confirmed by MS,IR,1H NMR and 13C NMR.",

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author = "Sun, {Cheng Hui} and Zhao, {Xin Qi}",

year = "2009",

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language = "English",

volume = "17",

pages = "1--3",

journal = "Hanneng Cailiao/Chinese Journal of Energetic Materials",

issn = "1006-9941",

publisher = "Chinese Academy of Engineering Physics",

number = "1",

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T1 - Nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo[ 5.5.3.02,6.04,10.08,12] pentadecane

AU - Sun, Cheng Hui

AU - Zhao, Xin Qi

PY - 2009/2

Y1 - 2009/2

N2 - In order to develop a new energetic materials, nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3 ,5 ,7 ,9,11-hexaazapentacyclo [5.5. 3. 02,6. 04,10. 08,12] pentadecane (I) was studied in detail. I was nitrolyzed selectively to 4-nitratomethyl-2,6, 8, 12-tetraacetyl-10-nitro-2,4,6,8,10,12-hexaazaisowurtzitane (II) with HNO3/Ac2O. While with mixture of nitric and sulfuric acids as nitration reagent, at 80 °C directly or at 15 °C 2 h firstly then 80 °C I was nitrolyzed to CL-20 or 4-nitratomethyl-2,6,8,10,12-pentanitrohezaazaisowurtzitane (III) respectively. II can also be nitrated to HI. The structures of two new hexaazaisowurtzitane derivatives (II and I) were confirmed by MS,IR,1H NMR and 13C NMR.

AB - In order to develop a new energetic materials, nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3 ,5 ,7 ,9,11-hexaazapentacyclo [5.5. 3. 02,6. 04,10. 08,12] pentadecane (I) was studied in detail. I was nitrolyzed selectively to 4-nitratomethyl-2,6, 8, 12-tetraacetyl-10-nitro-2,4,6,8,10,12-hexaazaisowurtzitane (II) with HNO3/Ac2O. While with mixture of nitric and sulfuric acids as nitration reagent, at 80 °C directly or at 15 °C 2 h firstly then 80 °C I was nitrolyzed to CL-20 or 4-nitratomethyl-2,6,8,10,12-pentanitrohezaazaisowurtzitane (III) respectively. II can also be nitrated to HI. The structures of two new hexaazaisowurtzitane derivatives (II and I) were confirmed by MS,IR,1H NMR and 13C NMR.

KW - 3,5,9, 11-tetraacetyl-14-oxo-1, 3, 5, 7, 9, 11-hexaazapentacyclo [5.5.3.0.0.0] pentadecane

KW - Hexaazaisowurtzitane derivative

KW - Organic chemistry

KW - Selective nitration

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M3 - Article

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JF - Hanneng Cailiao/Chinese Journal of Energetic Materials

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ER -

Nitrolysis of 3,5,9,11-tetraacetyl-14-oxo-1,3,5,7,9,11-hexaazapentacyclo[ 5.5.3.0^2,6.0^4,10.0^8,12] pentadecane

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