Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator

Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator

1,1′-Diamino-5,5′-bistetrazole (C2H4N10), a highly nitrogen-containing compound with promising energetic characteristics, is available through a classic organic reaction protocol applied on an inorganic azole system. This is the only Krapcho reaction on a carbamate system described in the literature...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2022-03, Vol.24 (8), p.1747-1751
Hauptverfasser: Benz, Maximilian, Klapötke, Thomas M, Stierstorfer, Jörg
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1751
container_issue 8
container_start_page 1747
container_title Organic letters
container_volume 24
creator Benz, Maximilian
Klapötke, Thomas M
Stierstorfer, Jörg
description 1,1′-Diamino-5,5′-bistetrazole (C2H4N10), a highly nitrogen-containing compound with promising energetic characteristics, is available through a classic organic reaction protocol applied on an inorganic azole system. This is the only Krapcho reaction on a carbamate system described in the literature so far. 1,1′-Diamino-5,5′-bistetrazole was extensively characterized through multinuclear spectroscopy, mass spectrometry, thermal analysis, and X-ray diffraction. The sensitivity values were measured, and detonation values were calculated. Its capability to initiate pentaerythritol tetranitrate (PETN) was successfully demonstrated.
doi_str_mv 10.1021/acs.orglett.2c00430
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2632797480</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2632797480</sourcerecordid><originalsourceid>FETCH-LOGICAL-a411t-a140dd0bce4196b8b4902936549886006343e7b8eec65d407005743c099f6ab53</originalsourceid><addsrcrecordid>eNp9kc1uEzEUhUcIREvhCZCQlyzq9Hpszw-7Km1pRBFI0PXojudOxpUzDrYjSFY8DQ_AI_EkTJTQJav7o3Pu0dWXZa8FzATk4gJNnPmwdJTSLDcASsKT7FToXPISdP70sS_gJHsR4wOAmDb18-xE6hwApDjNfn0IuDaDZ1dkMLT-x9Zhsn5kvmfXadg6Pp_WuMNE79iX7ZgGStawy_U6eDQDS_47ho6Jc_Hn529-ZXFlR8_1ud6PrY2JUsCdd8Rw7NgiRXafrLO7QwhGhuzWLgf-mULvw2Reso-U0PGbQMQWo00Wkw8vs2c9ukivjvUsu7-5_jq_5Xef3i_ml3cclRCJo1DQddAaUqIu2qpVNeS1LLSqq6oAKKSSVLYVkSl0p6AE0KWSBuq6L7DV8ix7e7g7vfdtQzE1KxsNOYcj-U1s8kLmZV2qCiapPEhN8DEG6pt1sCsM20ZAswfUTICaI6DmCGhyvTkGbNoVdY-ef0QmwcVBsHc_-E0Yp3__e_IvPpKh9g</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2632797480</pqid></control><display><type>article</type><title>Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator</title><source>American Chemical Society Journals</source><creator>Benz, Maximilian ; Klapötke, Thomas M ; Stierstorfer, Jörg</creator><creatorcontrib>Benz, Maximilian ; Klapötke, Thomas M ; Stierstorfer, Jörg</creatorcontrib><description>1,1′-Diamino-5,5′-bistetrazole (C2H4N10), a highly nitrogen-containing compound with promising energetic characteristics, is available through a classic organic reaction protocol applied on an inorganic azole system. This is the only Krapcho reaction on a carbamate system described in the literature so far. 1,1′-Diamino-5,5′-bistetrazole was extensively characterized through multinuclear spectroscopy, mass spectrometry, thermal analysis, and X-ray diffraction. The sensitivity values were measured, and detonation values were calculated. Its capability to initiate pentaerythritol tetranitrate (PETN) was successfully demonstrated.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.2c00430</identifier><identifier>PMID: 35200031</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2022-03, Vol.24 (8), p.1747-1751</ispartof><rights>2022 The Authors. Published by American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-a140dd0bce4196b8b4902936549886006343e7b8eec65d407005743c099f6ab53</citedby><cites>FETCH-LOGICAL-a411t-a140dd0bce4196b8b4902936549886006343e7b8eec65d407005743c099f6ab53</cites><orcidid>0000-0002-2105-1275 ; 0000-0003-3276-1157</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.2c00430$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.2c00430$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35200031$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Benz, Maximilian</creatorcontrib><creatorcontrib>Klapötke, Thomas M</creatorcontrib><creatorcontrib>Stierstorfer, Jörg</creatorcontrib><title>Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>1,1′-Diamino-5,5′-bistetrazole (C2H4N10), a highly nitrogen-containing compound with promising energetic characteristics, is available through a classic organic reaction protocol applied on an inorganic azole system. This is the only Krapcho reaction on a carbamate system described in the literature so far. 1,1′-Diamino-5,5′-bistetrazole was extensively characterized through multinuclear spectroscopy, mass spectrometry, thermal analysis, and X-ray diffraction. The sensitivity values were measured, and detonation values were calculated. Its capability to initiate pentaerythritol tetranitrate (PETN) was successfully demonstrated.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kc1uEzEUhUcIREvhCZCQlyzq9Hpszw-7Km1pRBFI0PXojudOxpUzDrYjSFY8DQ_AI_EkTJTQJav7o3Pu0dWXZa8FzATk4gJNnPmwdJTSLDcASsKT7FToXPISdP70sS_gJHsR4wOAmDb18-xE6hwApDjNfn0IuDaDZ1dkMLT-x9Zhsn5kvmfXadg6Pp_WuMNE79iX7ZgGStawy_U6eDQDS_47ho6Jc_Hn529-ZXFlR8_1ud6PrY2JUsCdd8Rw7NgiRXafrLO7QwhGhuzWLgf-mULvw2Reso-U0PGbQMQWo00Wkw8vs2c9ukivjvUsu7-5_jq_5Xef3i_ml3cclRCJo1DQddAaUqIu2qpVNeS1LLSqq6oAKKSSVLYVkSl0p6AE0KWSBuq6L7DV8ix7e7g7vfdtQzE1KxsNOYcj-U1s8kLmZV2qCiapPEhN8DEG6pt1sCsM20ZAswfUTICaI6DmCGhyvTkGbNoVdY-ef0QmwcVBsHc_-E0Yp3__e_IvPpKh9g</recordid><startdate>20220304</startdate><enddate>20220304</enddate><creator>Benz, Maximilian</creator><creator>Klapötke, Thomas M</creator><creator>Stierstorfer, Jörg</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2105-1275</orcidid><orcidid>https://orcid.org/0000-0003-3276-1157</orcidid></search><sort><creationdate>20220304</creationdate><title>Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator</title><author>Benz, Maximilian ; Klapötke, Thomas M ; Stierstorfer, Jörg</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-a140dd0bce4196b8b4902936549886006343e7b8eec65d407005743c099f6ab53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Benz, Maximilian</creatorcontrib><creatorcontrib>Klapötke, Thomas M</creatorcontrib><creatorcontrib>Stierstorfer, Jörg</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Benz, Maximilian</au><au>Klapötke, Thomas M</au><au>Stierstorfer, Jörg</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2022-03-04</date><risdate>2022</risdate><volume>24</volume><issue>8</issue><spage>1747</spage><epage>1751</epage><pages>1747-1751</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>1,1′-Diamino-5,5′-bistetrazole (C2H4N10), a highly nitrogen-containing compound with promising energetic characteristics, is available through a classic organic reaction protocol applied on an inorganic azole system. This is the only Krapcho reaction on a carbamate system described in the literature so far. 1,1′-Diamino-5,5′-bistetrazole was extensively characterized through multinuclear spectroscopy, mass spectrometry, thermal analysis, and X-ray diffraction. The sensitivity values were measured, and detonation values were calculated. Its capability to initiate pentaerythritol tetranitrate (PETN) was successfully demonstrated.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>35200031</pmid><doi>10.1021/acs.orglett.2c00430</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-2105-1275</orcidid><orcidid>https://orcid.org/0000-0003-3276-1157</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2022-03, Vol.24 (8), p.1747-1751
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2632797480
source American Chemical Society Journals
title Krapcho Decarboxylation of Ethyl-Carbazate: Synthetic Approach toward 1,1′-Diamino-5,5′-bistetrazole and Its Utilization as a High-Performing Metal-Free Initiator
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T20%3A35%3A23IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Krapcho%20Decarboxylation%20of%20Ethyl-Carbazate:%20Synthetic%20Approach%20toward%201,1%E2%80%B2-Diamino-5,5%E2%80%B2-bistetrazole%20and%20Its%20Utilization%20as%20a%20High-Performing%20Metal-Free%20Initiator&rft.jtitle=Organic%20letters&rft.au=Benz,%20Maximilian&rft.date=2022-03-04&rft.volume=24&rft.issue=8&rft.spage=1747&rft.epage=1751&rft.pages=1747-1751&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.2c00430&rft_dat=%3Cproquest_cross%3E2632797480%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2632797480&rft_id=info:pmid/35200031&rfr_iscdi=true