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Photochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivity

2013Journal article Open access
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dc.contributor.authorIsmael, Amin
dc.contributor.authorSerpa, C.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.date.accessioned2014-06-19T12:38:58Z
dc.date.available2014-06-19T12:38:58Z
dc.date.issued2013
dc.date.updated2014-06-12T09:02:14Z
dc.description.abstractThe photochemistry of tetrazolones derived from the carbocyclic allylic alcohols cyclohex-2-enol and 3-methylcyclohex-2-enol and from the natural terpene alcohol nerol was investigated in solution with the aim of assessing the effect of solvent and of structural constraints imposed by bulky allylic moieties on photoproduct selectivity and stability. Photolysis of tetrazolones derived from nerol and cyclohex-2-enol afforded the corresponding pyrimidinones as major products through a pathway that appears to be similar to that proposed for other 1-allyl-4-phenyl-1,4-dihydro-5H-tetrazol-5-ones derived from acyclic and unhindered allylic alcohols previously investigated but photolysis of the tetrazolone derived from the bulkier 3–methylcyclohex-2-enol 4c leads to formation of a benzimidazolone, indicating that, in this case, cyclization of the biradical formed upon extrusion of N2 involves the phenyl substituent and not the allylic moiety. Theoretical calculations (DFT(B3LYP)/3-21G*) were conducted to support the interpretation of the experimental results and mechanistic proposals. Laser flash photolysis experiments were conducted with the aim of clarifying the nature of the intermediate involved in the primary photocleavage process.por
dc.identifier.citationIsmael, Amin; Serpa, Carlos; Cristiano, M. Lurdes S. Photochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivity, Photochemical & Photobiological Sciences, 12, 2, 272-283, 2013.por
dc.identifier.doihttp://dx.doi.org/10.1007/s007750000164
dc.identifier.issn1474-905X
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4429
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherRoyal Society of Chemistrypor
dc.relation.publisherversionView Onlinepor
dc.titlePhotochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivitypor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage283por
oaire.citation.issue2por
oaire.citation.startPage272por
oaire.citation.titlePhotochemical & Photobiological Sciencespor
oaire.citation.volume12por
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.latestForDiscoveryb16751a6-748e-44b0-9c59-058cbd5b2cc3

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