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First observation of Chapman rearrangement of a pseudosaccharyl ether in the solid state: the thermal isomerization of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide revisited

2008Journal article Restricted access
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dc.contributor.authorAlmeida, R.
dc.contributor.authorGómez-Zavaglia, A.
dc.contributor.authorKaczor, A.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorEusébio, M. E. S.
dc.contributor.authorMaria, T. M. R.
dc.contributor.authorFausto, R.
dc.date.accessioned2014-06-09T13:29:53Z
dc.date.available2014-06-09T13:29:53Z
dc.date.issued2008
dc.date.updated2014-06-05T10:54:18Z
dc.description.abstract3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide, a pseudosaccharyl ether, was long ago known to undergo a thermal Chapman-like [1,30]-isomerization to the corresponding N-methyl pseudosaccharin at temperatures above its melting point (ca. 184 C) [Hettler H., Tetrahedron Lett. 1968, 15, 1793]. In the present study, it is shown that this rearrangement can also take place in the solid state, at temperatures as low as 150 C. This was the first observation of a Chapman-like [1,30]-isomerization in pseudosaccharyl ethers in the solid state. The study has been carried out by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry (DSC), and polarized light thermomicroscopy, complemented by theoretical methods.por
dc.identifier.citationAlmeida, R.; Gómez-Zavaglia, A.; Kaczor, A.; Cristiano, M.L.S.; Eusébio, M.E.S.; Maria, T.M.R.; Fausto, R. First observation of Chapman rearrangement of a pseudosaccharyl ether in the solid state: the thermal isomerization of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide revisited, Tetrahedron, 64, 15, 3296-3305, 2008.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.tet.2008.02.007
dc.identifier.issn0040-4020
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4257
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.subjectPseudosaccharinpor
dc.subjectChapman rearrangementpor
dc.subjectDFT calculationspor
dc.subjectInfrared spectroscopypor
dc.subjectDSCpor
dc.subjectThermomicroscopypor
dc.subject3-(Methoxy)-1,2-benzisothiazole 1,1-dioxidepor
dc.titleFirst observation of Chapman rearrangement of a pseudosaccharyl ether in the solid state: the thermal isomerization of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide revisitedpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage3305por
oaire.citation.issue15por
oaire.citation.startPage3296por
oaire.citation.titleTetrahedronpor
oaire.citation.volume64por
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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