Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/5023
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dc.contributor.authorAlmeida, R.-
dc.contributor.authorGómez-Zavaglia, Andrea-
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.accessioned2008-09-01T15:02:37Z-
dc.date.available2008-09-01T15:02:37Z-
dc.date.issued2008en_US
dc.identifier.citationTetrahedron. 64:15 (2008) 3296-3305en_US
dc.identifier.urihttp://hdl.handle.net/10316/5023-
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.en_US
dc.description.urihttp://www.sciencedirect.com/science/article/B6THR-4RSJDPJ-2/1/0f2df98480df370da897cdccab34054aen_US
dc.format.mimetypeaplication/PDFen
dc.language.isoengeng
dc.rightsopenAccesseng
dc.subjectPseudosaccharinen_US
dc.subject3-(Methoxy)-1,2-benzisothiazole 1,1-dioxideen_US
dc.subjectChapman rearrangementen_US
dc.subjectDFT calculationsen_US
dc.subjectInfrared spectroscopyen_US
dc.subjectThermomicroscopyen_US
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 revisiteden_US
dc.typearticleen_US
item.fulltextCom Texto completo-
item.grantfulltextopen-
item.languageiso639-1en-
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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