First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts

First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts

We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost qua...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European journal of organic chemistry 2004-04, Vol.2004 (7), p.1567-1571
Hauptverfasser: Boga, Carla, Del Vecchio, Erminia, Forlani, Luciano
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic substitution
Diazo compounds
Electrophilic substitution
NMR spectroscopy
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1571
container_issue 7
container_start_page 1567
container_title European journal of organic chemistry
container_volume 2004
creator Boga, Carla
Del Vecchio, Erminia
Forlani, Luciano
description We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost quantitative yields and are moderately stable compounds. From these covalent complexes, products of the azo‐coupling reaction may be obtained as salts or as free bases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
doi_str_mv 10.1002/ejoc.200300701
format Article
fullrecord <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_ejoc_200300701</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>EJOC200300701</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3911-cc31804761622fc44ae1a0e8ec51813ee2ec20851f07b90723f99b3988200e883</originalsourceid><addsrcrecordid>eNqFkM9OAjEQhzdGExG9eu5RExen22W3PZIV_BOjCWLw1pQyq4Wla9pFhCfwqo_ok7gEY7h5mt9k5ptJviA4ptCiANE5TkrdigAYQAp0J2hQECKERMBunWMWh1Swp_3gwPsJAIgkoY3gs2ecr0j3zYzRaiR56cjwBQtlx-TaVuhmODaqQk-MJZ1VGWbl_LUw9pn0UenKlNaT74-vrW6E1QLREnrGztrhwBl_Ul8opstCzYwtT0doV2iRrD90XJ3q6aq0Zj4jD6qo_GGwl6vC49FvbQaPve4guwpv7y-vs85tqJmgNNSaUQ5xmtAkinIdxwqpAuSo25RThhihjoC3aQ7pSEAasVyIEROc14qQc9YMWpu72pXeO8zlqzMz5ZaSglwLlWuh8k9oDYgNsDAFLv_Zlt2b-2ybDTes8RW-_7HKTWWSsrQth3eXsp8lvYsBj-UV-wF45otL</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Boga, Carla ; Del Vecchio, Erminia ; Forlani, Luciano</creator><creatorcontrib>Boga, Carla ; Del Vecchio, Erminia ; Forlani, Luciano</creatorcontrib><description>We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost quantitative yields and are moderately stable compounds. From these covalent complexes, products of the azo‐coupling reaction may be obtained as salts or as free bases. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200300701</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aromatic substitution ; Diazo compounds ; Electrophilic substitution ; NMR spectroscopy</subject><ispartof>European journal of organic chemistry, 2004-04, Vol.2004 (7), p.1567-1571</ispartof><rights>Copyright © 2004 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3911-cc31804761622fc44ae1a0e8ec51813ee2ec20851f07b90723f99b3988200e883</citedby><cites>FETCH-LOGICAL-c3911-cc31804761622fc44ae1a0e8ec51813ee2ec20851f07b90723f99b3988200e883</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200300701$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45551</link.rule.ids></links><search><creatorcontrib>Boga, Carla</creatorcontrib><creatorcontrib>Del Vecchio, Erminia</creatorcontrib><creatorcontrib>Forlani, Luciano</creatorcontrib><title>First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost quantitative yields and are moderately stable compounds. From these covalent complexes, products of the azo‐coupling reaction may be obtained as salts or as free bases. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</description><subject>Aromatic substitution</subject><subject>Diazo compounds</subject><subject>Electrophilic substitution</subject><subject>NMR spectroscopy</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkM9OAjEQhzdGExG9eu5RExen22W3PZIV_BOjCWLw1pQyq4Wla9pFhCfwqo_ok7gEY7h5mt9k5ptJviA4ptCiANE5TkrdigAYQAp0J2hQECKERMBunWMWh1Swp_3gwPsJAIgkoY3gs2ecr0j3zYzRaiR56cjwBQtlx-TaVuhmODaqQk-MJZ1VGWbl_LUw9pn0UenKlNaT74-vrW6E1QLREnrGztrhwBl_Ul8opstCzYwtT0doV2iRrD90XJ3q6aq0Zj4jD6qo_GGwl6vC49FvbQaPve4guwpv7y-vs85tqJmgNNSaUQ5xmtAkinIdxwqpAuSo25RThhihjoC3aQ7pSEAasVyIEROc14qQc9YMWpu72pXeO8zlqzMz5ZaSglwLlWuh8k9oDYgNsDAFLv_Zlt2b-2ybDTes8RW-_7HKTWWSsrQth3eXsp8lvYsBj-UV-wF45otL</recordid><startdate>200404</startdate><enddate>200404</enddate><creator>Boga, Carla</creator><creator>Del Vecchio, Erminia</creator><creator>Forlani, Luciano</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200404</creationdate><title>First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts</title><author>Boga, Carla ; Del Vecchio, Erminia ; Forlani, Luciano</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3911-cc31804761622fc44ae1a0e8ec51813ee2ec20851f07b90723f99b3988200e883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Aromatic substitution</topic><topic>Diazo compounds</topic><topic>Electrophilic substitution</topic><topic>NMR spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Boga, Carla</creatorcontrib><creatorcontrib>Del Vecchio, Erminia</creatorcontrib><creatorcontrib>Forlani, Luciano</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Boga, Carla</au><au>Del Vecchio, Erminia</au><au>Forlani, Luciano</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2004-04</date><risdate>2004</risdate><volume>2004</volume><issue>7</issue><spage>1567</spage><epage>1571</epage><pages>1567-1571</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>We have investigated reactions between 1,3,5‐tris(1‐piperidyl)benzene and 1,3,5‐tris(4‐morpholinyl)benzene and 4‐substituted arenediazonium tetrafluoroborate salts, mainly by NMR spectroscopic measurements. The main products are σ complexes (Wheland‐like intermediates) which are formed in almost quantitative yields and are moderately stable compounds. From these covalent complexes, products of the azo‐coupling reaction may be obtained as salts or as free bases. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2004)</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200300701</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European journal of organic chemistry, 2004-04, Vol.2004 (7), p.1567-1571
issn 1434-193X
1099-0690
language eng
recordid cdi_crossref_primary_10_1002_ejoc_200300701
source Wiley Online Library Journals Frontfile Complete
subjects Aromatic substitution
Diazo compounds
Electrophilic substitution
NMR spectroscopy
title First Evidence for Wheland Intermediates in Azo-Coupling Reactions − Reactions between 1,3,5-Tris(dialkylamino)benzene and Arenediazonium Salts
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T05%3A40%3A26IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=First%20Evidence%20for%20Wheland%20Intermediates%20in%20Azo-Coupling%20Reactions%20%E2%88%92%20Reactions%20between%201,3,5-Tris(dialkylamino)benzene%20and%20Arenediazonium%20Salts&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Boga,%20Carla&rft.date=2004-04&rft.volume=2004&rft.issue=7&rft.spage=1567&rft.epage=1571&rft.pages=1567-1571&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.200300701&rft_dat=%3Cwiley_cross%3EEJOC200300701%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true