Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System
This study presents the synthesis and characterization of a fused, tricyclic 1,2,3,4‐tetrazine ring system. The molecule is synthesized in a three‐step process from 5,5′‐dinitro‐bis,1,2,4‐triazole via a di‐N‐amino compound. Oxidation to form the azo‐coupled fused tricyclic 1,2,3,4‐tetrazine is achie...
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2015-10, Vol.54 (44), p.12973-12975 |
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| container_title | Angewandte Chemie (International ed.) |
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| creator | Chavez, David E. Bottaro, Jeffery C. Petrie, Mark Parrish, Damon A. |
| description | This study presents the synthesis and characterization of a fused, tricyclic 1,2,3,4‐tetrazine ring system. The molecule is synthesized in a three‐step process from 5,5′‐dinitro‐bis,1,2,4‐triazole via a di‐N‐amino compound. Oxidation to form the azo‐coupled fused tricyclic 1,2,3,4‐tetrazine is achieved using tert‐butyl hypochlorite as the oxidant. The di‐N‐amino compound and the desired fused tricyclic 1,2,3,4‐triazine display interesting thermal behavior and are predicted to be high‐performance energetic materials.
Ring of fire: Double N‐amination of the bis(tetraethylammonium) salt of 3,3′‐dinitro‐5,5′‐bi‐1,2,4‐triazole results in a thermally stable di‐N‐aminated energetic material that is insensitive to impact, spark, and friction. Subsequent oxidation leads to a fused, tricyclic 1,2,3,4‐tetrazine ring system (see figure) with excellent density and explosive performance properties. |
| doi_str_mv | 10.1002/anie.201506744 |
| format | Article |
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Ring of fire: Double N‐amination of the bis(tetraethylammonium) salt of 3,3′‐dinitro‐5,5′‐bi‐1,2,4‐triazole results in a thermally stable di‐N‐aminated energetic material that is insensitive to impact, spark, and friction. Subsequent oxidation leads to a fused, tricyclic 1,2,3,4‐tetrazine ring system (see figure) with excellent density and explosive performance properties.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201506744</identifier><identifier>PMID: 26480332</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>1,2,3,4‐tetrazines ; 1,2,4‐triazoles ; 4-tetrazines ; 4-triazoles ; amination ; Chemical synthesis ; Density ; Energetic materials ; Explosions ; Fires ; Friction ; Oxidants ; Oxidation ; Oxidizing agents ; Synthesis ; Thermodynamic properties ; Triazine</subject><ispartof>Angewandte Chemie (International ed.), 2015-10, Vol.54 (44), p.12973-12975</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright Wiley Subscription Services, Inc. Oct 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6464-83a857f6910344f2864540ceb396e47f44e3a02093a8012a3b16a1a6006045053</citedby><cites>FETCH-LOGICAL-c6464-83a857f6910344f2864540ceb396e47f44e3a02093a8012a3b16a1a6006045053</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201506744$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201506744$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26480332$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1492654$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Chavez, David E.</creatorcontrib><creatorcontrib>Bottaro, Jeffery C.</creatorcontrib><creatorcontrib>Petrie, Mark</creatorcontrib><creatorcontrib>Parrish, Damon A.</creatorcontrib><creatorcontrib>Los Alamos National Lab. (LANL), Los Alamos, NM (United States)</creatorcontrib><title>Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System</title><title>Angewandte Chemie (International ed.)</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>This study presents the synthesis and characterization of a fused, tricyclic 1,2,3,4‐tetrazine ring system. The molecule is synthesized in a three‐step process from 5,5′‐dinitro‐bis,1,2,4‐triazole via a di‐N‐amino compound. Oxidation to form the azo‐coupled fused tricyclic 1,2,3,4‐tetrazine is achieved using tert‐butyl hypochlorite as the oxidant. The di‐N‐amino compound and the desired fused tricyclic 1,2,3,4‐triazine display interesting thermal behavior and are predicted to be high‐performance energetic materials.
Ring of fire: Double N‐amination of the bis(tetraethylammonium) salt of 3,3′‐dinitro‐5,5′‐bi‐1,2,4‐triazole results in a thermally stable di‐N‐aminated energetic material that is insensitive to impact, spark, and friction. Subsequent oxidation leads to a fused, tricyclic 1,2,3,4‐tetrazine ring system (see figure) with excellent density and explosive performance properties.</description><subject>1,2,3,4‐tetrazines</subject><subject>1,2,4‐triazoles</subject><subject>4-tetrazines</subject><subject>4-triazoles</subject><subject>amination</subject><subject>Chemical synthesis</subject><subject>Density</subject><subject>Energetic materials</subject><subject>Explosions</subject><subject>Fires</subject><subject>Friction</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Synthesis</subject><subject>Thermodynamic properties</subject><subject>Triazine</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqN0U1vEzEQBuAVAtFSuHJEFlw4ZMP423tsS1sqVUVKgzhajjNLXPaj2Btg-fU42hIhDsBp5vDMK43eonhOYU4B2BvXBZwzoBKUFuJBcUgloyXXmj_Mu-C81EbSg-JJSrfZGwPqcXHAlDDAOTssFjdjN2wwhURctybLDcbWNeQEN-5r6CPpa-LI-TbhekaWMfjRN8ETOmMzPhPlEofofoQOySJ0n8jNmAZsnxaPatckfHY_j4oP52fL03fl1fuLy9Pjq9IroURpuDNS16qiwIWomVFCCvC44pVCoWshkDtgUGUHlDm-ospRpwAUCAmSHxUvp9w-DcEmHwb0G993HfrBUlExJUVGryd0F_svW0yDbUPy2DSuw36bLNUauGZayv-gTALTQHWmr_6gt_02dvlby6RilAujzN9UzmIVFXlkNZ-Uj31KEWt7F0Pr4mgp2F3Hdtex3XecD17cx25XLa73_FepGVQT-BYaHP8RZ4-vL89-Dy-n25Cr_L6_dfGzVZpraT9eX9iFPDFvd4vmPwH47Lr1</recordid><startdate>20151026</startdate><enddate>20151026</enddate><creator>Chavez, David E.</creator><creator>Bottaro, Jeffery C.</creator><creator>Petrie, Mark</creator><creator>Parrish, Damon A.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><general>Wiley</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>OTOTI</scope></search><sort><creationdate>20151026</creationdate><title>Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System</title><author>Chavez, David E. ; Bottaro, Jeffery C. ; Petrie, Mark ; Parrish, Damon A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6464-83a857f6910344f2864540ceb396e47f44e3a02093a8012a3b16a1a6006045053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>1,2,3,4‐tetrazines</topic><topic>1,2,4‐triazoles</topic><topic>4-tetrazines</topic><topic>4-triazoles</topic><topic>amination</topic><topic>Chemical synthesis</topic><topic>Density</topic><topic>Energetic materials</topic><topic>Explosions</topic><topic>Fires</topic><topic>Friction</topic><topic>Oxidants</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Synthesis</topic><topic>Thermodynamic properties</topic><topic>Triazine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chavez, David E.</creatorcontrib><creatorcontrib>Bottaro, Jeffery C.</creatorcontrib><creatorcontrib>Petrie, Mark</creatorcontrib><creatorcontrib>Parrish, Damon A.</creatorcontrib><creatorcontrib>Los Alamos National Lab. (LANL), Los Alamos, NM (United States)</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>OSTI.GOV</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chavez, David E.</au><au>Bottaro, Jeffery C.</au><au>Petrie, Mark</au><au>Parrish, Damon A.</au><aucorp>Los Alamos National Lab. (LANL), Los Alamos, NM (United States)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-10-26</date><risdate>2015</risdate><volume>54</volume><issue>44</issue><spage>12973</spage><epage>12975</epage><pages>12973-12975</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>This study presents the synthesis and characterization of a fused, tricyclic 1,2,3,4‐tetrazine ring system. The molecule is synthesized in a three‐step process from 5,5′‐dinitro‐bis,1,2,4‐triazole via a di‐N‐amino compound. Oxidation to form the azo‐coupled fused tricyclic 1,2,3,4‐tetrazine is achieved using tert‐butyl hypochlorite as the oxidant. The di‐N‐amino compound and the desired fused tricyclic 1,2,3,4‐triazine display interesting thermal behavior and are predicted to be high‐performance energetic materials.
Ring of fire: Double N‐amination of the bis(tetraethylammonium) salt of 3,3′‐dinitro‐5,5′‐bi‐1,2,4‐triazole results in a thermally stable di‐N‐aminated energetic material that is insensitive to impact, spark, and friction. Subsequent oxidation leads to a fused, tricyclic 1,2,3,4‐tetrazine ring system (see figure) with excellent density and explosive performance properties.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26480332</pmid><doi>10.1002/anie.201506744</doi><tpages>3</tpages><edition>International ed. in English</edition><oa>free_for_read</oa></addata></record> |
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| subjects | 1,2,3,4‐tetrazines 1,2,4‐triazoles 4-tetrazines 4-triazoles amination Chemical synthesis Density Energetic materials Explosions Fires Friction Oxidants Oxidation Oxidizing agents Synthesis Thermodynamic properties Triazine |
| title | Synthesis and Thermal Behavior of a Fused, Tricyclic 1,2,3,4-Tetrazine Ring System |
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