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The thermal sigmatropic isomerization of pseudosaccharyl crotyl ether

2013Journal article Restricted access
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dc.contributor.authorCabral, Lília
dc.contributor.authorMaria, T. M. R.
dc.contributor.authorMartelo, L.
dc.contributor.authorEusébio, M. E. S.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorFausto, R.
dc.date.accessioned2014-06-06T15:28:26Z
dc.date.available2014-06-06T15:28:26Z
dc.date.issued2013
dc.date.updated2014-05-30T16:02:43Z
dc.description.abstractThe thermally induced sigmatropic isomerization of the pseudosaccharyl crotyl ether, 3-(E)-but-2-enoxy)-1,2-benzisothiazole 1,1-dioxide (CBID), has been investigated by using temperature dependent infrared spectroscopy, differential scanning calorimetry (DSC), and polarized light thermomicroscopy. The reaction can take place in both melted and crystalline phases, affording the product resulting from the [3,30] migration of the allylic system from O to N, 2-(E)-1-methylprop-2-en-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (CBIOD). In the melt, the activation energy of the process was determined as being 49.1 5.3 kJ mol 1, with k¼(22.2 0.6) 104 s 1 at 140 C. In the solid state, at 110 C, the rate constant drops by one order of magnitude [k¼(1.46 0.07) 104 s 1]. The enthalpy of reaction, determined by DSC, is DrxH¼ 27.0 0.8 kJ mol 1. Assignments were proposed for the infrared spectra of the observed neat condensed phases of the two compounds.por
dc.identifier.citationCabral, L.I.L.; Maria, T.M.R.; Martelo, L.; Eusébio, M.E.S.; Cristiano, M.L.S.; Fausto, R. The thermal sigmatropic isomerization of pseudosaccharyl crotyl ether, Tetrahedron, 69, 2, 810-815, 2013.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.tet.2012.10.100
dc.identifier.issn0040-4020
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4227
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subjectSaccharinpor
dc.subject3-(E)-(But-2-enoxy)-1,2-benzisothiazolepor
dc.subject1,1-dioxidepor
dc.subjectSigmatropic rearrangementpor
dc.subjectInfrared spectroscopypor
dc.subjectDSCpor
dc.subjectThermomicroscopypor
dc.titleThe thermal sigmatropic isomerization of pseudosaccharyl crotyl etherpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage815por
oaire.citation.issue2por
oaire.citation.startPage810por
oaire.citation.titleTetrahedronpor
oaire.citation.volume69por
person.familyNameCabral
person.familyNameCristiano
person.givenNameLília
person.givenNameMaria de Lurdes
person.identifier.ciencia-id3510-24A8-36B6
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0001-9362-8128
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridM-4279-2013
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id9238724800
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication175a6aa3-9993-480b-9663-ed083a17eedf
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscovery175a6aa3-9993-480b-9663-ed083a17eedf

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