Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine

Yongxing Tang; Chunlin He; Ping Yin; Gregory H. Imler; Damon A. Parrish; Jean'ne M. Shreeve

doi:10.1002/ejoc.201800347

Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine

Yongxing Tang, Chunlin He, Ping Yin, Gregory H. Imler, Damon A. Parrish, Jean'ne M. Shreeve^*

^*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

Despite the high potential of the azo-coupled fused tricyclic 1,2,3,4-tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di-N-amino compound 1 with tert-butyl hypochlorite (tBuOCl) gives rise to the unexpected chloro-substituted compound 2, which behaves as a precursor to the structurally attractive diazido/nitro-substituted fused tricyclic 1,2,3,4-tetrazine 3. The structure is well characterized and is supported by single-crystal X-ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.

Original language	English
Pages (from-to)	2273-2276
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.201800347
Publication status	Published - 24 May 2018
Externally published	Yes

Keywords

Azido group
Azo coupling reaction
Energetic materials
Imidazole
Nitrogen heterocycles

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10.1002/ejoc.201800347

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title = "Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine",

abstract = "Despite the high potential of the azo-coupled fused tricyclic 1,2,3,4-tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di-N-amino compound 1 with tert-butyl hypochlorite (tBuOCl) gives rise to the unexpected chloro-substituted compound 2, which behaves as a precursor to the structurally attractive diazido/nitro-substituted fused tricyclic 1,2,3,4-tetrazine 3. The structure is well characterized and is supported by single-crystal X-ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.",

keywords = "Azido group, Azo coupling reaction, Energetic materials, Imidazole, Nitrogen heterocycles",

author = "Yongxing Tang and Chunlin He and Ping Yin and Imler, \{Gregory H.\} and Parrish, \{Damon A.\} and Shreeve, \{Jean'ne M.\}",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = may,

day = "24",

doi = "10.1002/ejoc.201800347",

language = "English",

volume = "2018",

pages = "2273--2276",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

number = "19",

}

TY - JOUR

T1 - Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine

AU - Tang, Yongxing

AU - He, Chunlin

AU - Yin, Ping

AU - Imler, Gregory H.

AU - Parrish, Damon A.

AU - Shreeve, Jean'ne M.

PY - 2018/5/24

Y1 - 2018/5/24

N2 - Despite the high potential of the azo-coupled fused tricyclic 1,2,3,4-tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di-N-amino compound 1 with tert-butyl hypochlorite (tBuOCl) gives rise to the unexpected chloro-substituted compound 2, which behaves as a precursor to the structurally attractive diazido/nitro-substituted fused tricyclic 1,2,3,4-tetrazine 3. The structure is well characterized and is supported by single-crystal X-ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.

AB - Despite the high potential of the azo-coupled fused tricyclic 1,2,3,4-tetrazine ring system in energetic materials, there are only very limited examples of such a scaffold. The oxidation of di-N-amino compound 1 with tert-butyl hypochlorite (tBuOCl) gives rise to the unexpected chloro-substituted compound 2, which behaves as a precursor to the structurally attractive diazido/nitro-substituted fused tricyclic 1,2,3,4-tetrazine 3. The structure is well characterized and is supported by single-crystal X-ray diffraction. Compound 3 was found to be a highly energetic and sensitive explosive.

KW - Azido group

KW - Azo coupling reaction

KW - Energetic materials

KW - Imidazole

KW - Nitrogen heterocycles

UR - https://www.scopus.com/pages/publications/85047665048

U2 - 10.1002/ejoc.201800347

DO - 10.1002/ejoc.201800347

M3 - Article

AN - SCOPUS:85047665048

SN - 1434-193X

VL - 2018

SP - 2273

EP - 2276

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 19

ER -

Energetic Functionalized Azido/Nitro Imidazole Fused 1,2,3,4-Tetrazine

Abstract

Keywords

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