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Sigmatropic rearrangements in 5-allyloxytetrazoles

2011Journal article Open access
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dc.contributor.authorFrija, L.
dc.contributor.authorReva, I. D.
dc.contributor.authorIsmael, Amin
dc.contributor.authorCoelho, Daniela
dc.contributor.authorFausto, R.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.date.accessioned2014-06-07T11:08:59Z
dc.date.available2014-06-07T11:08:59Z
dc.date.issued2011
dc.date.updated2014-06-05T09:01:02Z
dc.description.abstractMechanisms of thermal isomerization of allyl tetrazolyl ethers derived from the carbocyclic allylic alcohols cyclohex-2-enol and 3-methylcyclohex-2-enol and from the natural terpene alcohol nerol were investigated. In the process of the syntheses of the three 1-aryl-5-allyloxytetrazoles, their rapid isomerization to the corresponding 1-aryl-4-allyltetrazol-5-ones occurred. The experiments showed that the imidates rearrange exclusively through a [3,3¢]-sigmatropic migration of the allylic system from O to N, with inversion. Mechanistic proposals are based on product analysis and extensive quantum chemical calculations at the DFT(B3LYP) and MP2 levels, on O-allyl and N-allyl isomers and on putative transition state structures for [1,3¢]- and [3,3¢]-sigmatropic migrations. The experimental observations could be only explained on the basis of the MP2/6-31G(d,p) calculations that favoured the [3,3¢]-sigmatropic migrations, yielding lower energies both for the transition states and for the final isomerization products.por
dc.identifier.citationFrija, Luís M. T.; Reva, Igor; Ismael, Amin; Coelho, Daniela V.; Fausto, Rui; Cristiano, M. Lurdes S. Sigmatropic rearrangements in 5-allyloxytetrazoles, Organic & Biomolecular Chemistry, 9, 17, 6040-6054, 2011.por
dc.identifier.doihttp://dx.doi.org/10.1039/c1ob05460k
dc.identifier.issn1477-0520
dc.identifier.otherAUT: MCR00716
dc.identifier.urihttp://hdl.handle.net/10400.1/4243
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherRoyal Society of Chemistrypor
dc.relation.publisherversionView Article Onlinepor
dc.titleSigmatropic rearrangements in 5-allyloxytetrazolespor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage6054por
oaire.citation.issue17por
oaire.citation.startPage6040por
oaire.citation.titleOrganic & Biomolecular Chemistrypor
oaire.citation.volume9por
person.familyNameIsmael
person.familyNameCristiano
person.givenNameAmin
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-7346-5998
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridA-8153-2013
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id35203489500
person.identifier.scopus-author-id9238724800
rcaap.rightsopenAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublicationfa01ef7f-7a2a-4f74-a405-714360b862f3
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscoveryfa01ef7f-7a2a-4f74-a405-714360b862f3

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