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Palladium-catalysed reduction of heteroaromatic naphthyl ethers: structural effects on reactivity

2005Journal article Restricted access
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dc.contributor.authorFrija, L.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorGuimarães, Emanuel M. O.
dc.contributor.authorMartins, Nelson C.
dc.contributor.authorLoureiro, Rui M. S.
dc.contributor.authorBickley, Jamie F.
dc.date.accessioned2014-06-11T12:54:36Z
dc.date.available2014-06-11T12:54:36Z
dc.date.issued2005
dc.date.updated2014-06-05T09:59:48Z
dc.description.abstractTetrazolyl and benzisothiazolyl naphthylmethylic ethers 3 and 4(a–e) are stable crystalline compounds that can be synthesised in high yields by reaction of the corresponding naphthyl methanols (1a–e) with the derivatizing agents 2a and 2b. Experimental conditions for palladium-catalysed hydrogenolysis of ethers 3, 4, with a hydrogen donor and with molecular hydrogen, were investigated. Analysis of the structure and reactivity indicates that naphthylmethylic ethers 3 and 4 are structurally similar to the corresponding benzyloxyderivatives around the ether bond but exhibit different reactivity. Structural analysis for these compounds is based on crystallographic structure determinations, for 5-(2-naphthylmethoxy)-1-phenyltetrazole (3a) and 3-(2-naphthylmethoxy)-1,2-benzisothiazole 1,1-dioxide (4a), and molecular orbital DFT(B3LYP)/6-311G(d) calculations, for all ethers. It can be concluded from this investigation that 5-chloro-1-phenyltetrazole 2a acts as a better derivatizing agent for naphthyl methanols than 3-chloro-1,2-benzisothiazole-11-dioxide 2b, this contrasting with what has been observed with phenols, allylic and benzylic alcohols.por
dc.identifier.citationFrija, Luís M.T.; Cristiano, M. Lurdes S.; Guimarães, Emanuel M.O.; Martins, Nelson C.; Loureiro, Rui. M.S.; Bickley, Jamie F. Palladium-catalysed reduction of heteroaromatic naphthyl ethers: Structural effects on reactivity, Journal of Molecular Catalysis A: Chemical, 242, 1-2, 241-250, 2005.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.molcata.2005.08.022
dc.identifier.issn1381-1169
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4266
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subjectTetrazolespor
dc.subjectBenzisothiazolespor
dc.subjectNaphthylmethylic etherspor
dc.subjectPalladium-on-charcoalpor
dc.subjectHydrogenolysispor
dc.subjectHydrogenationpor
dc.titlePalladium-catalysed reduction of heteroaromatic naphthyl ethers: structural effects on reactivitypor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage250por
oaire.citation.issue1-2por
oaire.citation.startPage241por
oaire.citation.titleJournal of Molecular Catalysis A: Chemicalpor
oaire.citation.volume242por
person.familyNameCristiano
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id9238724800
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscoveryb16751a6-748e-44b0-9c59-058cbd5b2cc3

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