Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/17941
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dc.contributor.authorAlmeida, R.-
dc.contributor.authorGómez-Zavaglia, A.-
dc.contributor.authorKaczor, A.-
dc.contributor.authorCristiano, M.L.S.-
dc.contributor.authorEusébio, M.E.S.-
dc.contributor.authorMaria, T.M.R.-
dc.contributor.authorFausto, R.-
dc.date.accessioned2011-12-16T11:21:50Z-
dc.date.available2011-12-16T11:21:50Z-
dc.date.issued2008-04-
dc.identifier.urihttp://hdl.handle.net/10316/17941-
dc.description.abstract3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide, a pseudosaccharyl ether, was long ago known to undergo a thermal Chapman-like [1,3′]-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 [1,3′]-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. Graphical abstractpor
dc.language.isoengpor
dc.publisherElsevierpor
dc.rightsopenAccesspor
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.typearticlepor
degois.publication.firstPage3296por
degois.publication.lastPage3305por
degois.publication.titleTetrahedronpor
dc.peerreviewedYespor
dc.identifier.doi10.1016/j.tet.2008.02.007-
degois.publication.volume64por
item.languageiso639-1en-
item.fulltextCom Texto completo-
item.grantfulltextopen-
crisitem.author.deptFaculdade de Ciências e Tecnologia, Universidade de Coimbra-
crisitem.author.parentdeptUniversidade de Coimbra-
crisitem.author.researchunitCoimbra Chemistry Center-
crisitem.author.orcid0000-0002-8264-6854-
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais
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