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Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/

2002Journal article Open access
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dc.contributor.authorAraujo, Nuna C. P.
dc.contributor.authorBarroca, Pedro M. M.
dc.contributor.authorBickley, Jamie F.
dc.contributor.authorBrigas, Amadeu
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorJohnstone, Robert A. W.
dc.contributor.authorLoureiro, Rui M. S.
dc.contributor.authorPena, Paula C. A.
dc.date.accessioned2014-06-07T12:56:06Z
dc.date.available2014-06-07T12:56:06Z
dc.date.issued2002
dc.date.updated2014-06-05T09:48:24Z
dc.description.abstractIn contrast to the known thermal, exclusively [3,3], O- to N- rearrangement of allyl groups in phenyltetrazoles (1, Scheme 1), the comparable migration of the allyl group in pseudosaccharyl ethers (3; Scheme 2) has been shown to proceed through both [1,3]- and [3,3]-mechanisms, 4, 5; for the pseudosaccharyl derivative of the natural product myrtenol (6; Scheme 3) only the product 7 of a [1,3]-shift has been observed; crystallographic data and theoretical calculations provide an explanation of this ease of [1,3]-isomerization and the observed selectivity as being due to conformational constraints and electronic factors.por
dc.identifier.citationAraújo, Nuna C. P.; Barroca, Pedro M. M.; Bickley, Jamie F.; Brigas, Amadeu F.; Cristiano, M. Lurdes S.; Johnstone, Robert A. W.; Loureiro, Rui M. S.; Pena, Paula C. A. Structural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/, Journal of the Chemical Society, Perkin Transactions 1, 9, 1213-1219, 2002.por
dc.identifier.doihttp://dx.doi.org/10.1039/b102674g
dc.identifier.issn1472-7781
dc.identifier.otherAUT: ABR00608; MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4250
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherRoyal Society of Chemistrypor
dc.relation.publisherversionView Article Onlinepor
dc.titleStructural effects on sigmatropic shifts in heteroaromatic allyl ethersElectronic supplementary information (ESI) available: selected crystal data for compound 7. See http://www.rsc.org/suppdata/p1/b1/b102674g/por
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage1219por
oaire.citation.issue9por
oaire.citation.startPage1213por
oaire.citation.titlePerkin Transactionspor
oaire.citation.volume1por
person.familyNameAraujo
person.familyNameBrigas
person.familyNameCristiano
person.givenNameNuna
person.givenNameAmadeu
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-7602-0150
person.identifier.orcid0000-0003-4875-4453
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridN-8531-2013
person.identifier.ridE-1897-2012
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id6701450565
person.identifier.scopus-author-id9238724800
rcaap.rightsopenAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication3423e71b-934d-4da7-9c81-4e56c7930252
relation.isAuthorOfPublication7b0e903c-4730-497c-a012-f9fa0fc5e6dc
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscoveryb16751a6-748e-44b0-9c59-058cbd5b2cc3

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