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Article: The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms

TitleThe coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms
Authors
Jones, GOLi, XHayden, AEHouk, KNDanishefsky, SJ
Issue Date2008
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.html
Citation
Organic Letters, 2008, v. 10 n. 18, p. 4093-4096 How to Cite?
DOI: http://dx.doi.org/10.1021/ol8016287
Abstract(Chemical Equation Presented) Mechanisms for the recently described reactions of isonitriles with carboxylic acids (Li, X.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 5446) are explored with the B3LYP density functional method. The mechanism involves the formation of a carboxylate mixed formimidic anhydride intermediate via a concerted mechanism. This intermediate is then transformed to an N-formylamide by a concerted pseudopericyclic [1,3]-acyl shift. Mechanisms involving zwitterions or diradicals are discounted. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168329
ISSN
1523-7060
2021 Impact Factor: 6.072
2020 SCImago Journal Rankings: 1.940
ISI Accession Number ID
WOS:000259197600041
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorJones, GOen_US
dc.contributor.authorLi, Xen_US
dc.contributor.authorHayden, AEen_US
dc.contributor.authorHouk, KNen_US
dc.contributor.authorDanishefsky, SJen_US
dc.date.accessioned2012-10-08T03:17:40Z-
dc.date.available2012-10-08T03:17:40Z-
dc.date.issued2008en_US
dc.identifier.citationOrganic Letters, 2008, v. 10 n. 18, p. 4093-4096en_US
dc.identifier.issn1523-7060en_US
dc.identifier.urihttp://hdl.handle.net/10722/168329-
dc.description.abstract(Chemical Equation Presented) Mechanisms for the recently described reactions of isonitriles with carboxylic acids (Li, X.; Danishefsky, S. J. J. Am. Chem. Soc. 2008, 130, 5446) are explored with the B3LYP density functional method. The mechanism involves the formation of a carboxylate mixed formimidic anhydride intermediate via a concerted mechanism. This intermediate is then transformed to an N-formylamide by a concerted pseudopericyclic [1,3]-acyl shift. Mechanisms involving zwitterions or diradicals are discounted. © 2008 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/orlef7/index.htmlen_US
dc.relation.ispartofOrganic Lettersen_US
dc.titleThe coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanismsen_US
dc.typeArticleen_US
dc.identifier.emailLi, X:xuechenl@hku.hken_US
dc.identifier.authorityLi, X=rp00742en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ol8016287en_US
dc.identifier.pmid18707109-
dc.identifier.scopuseid_2-s2.0-53549110712en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-53549110712&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume10en_US
dc.identifier.issue18en_US
dc.identifier.spage4093en_US
dc.identifier.epage4096en_US
dc.identifier.isiWOS:000259197600041-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridJones, GO=8688956600en_US
dc.identifier.scopusauthoridLi, X=24168958800en_US
dc.identifier.scopusauthoridHayden, AE=14054001000en_US
dc.identifier.scopusauthoridHouk, KN=7102149960en_US
dc.identifier.scopusauthoridDanishefsky, SJ=7202925243en_US
dc.identifier.issnl1523-7052-

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