Please use this identifier to cite or link to this item:
https://hdl.handle.net/10316/17941
DC Field | Value | Language |
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dc.contributor.author | Almeida, R. | - |
dc.contributor.author | Gómez-Zavaglia, A. | - |
dc.contributor.author | Kaczor, A. | - |
dc.contributor.author | Cristiano, M. L. S. | - |
dc.contributor.author | Eusébio, M. E. S. | - |
dc.contributor.author | Maria, T. M. R. | - |
dc.contributor.author | Fausto, R. | - |
dc.date.accessioned | 2011-12-16T11:21:50Z | - |
dc.date.available | 2011-12-16T11:21:50Z | - |
dc.date.issued | 2008-04 | - |
dc.identifier.uri | https://hdl.handle.net/10316/17941 | - |
dc.description.abstract | 3-(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 abstract | por |
dc.language.iso | eng | por |
dc.publisher | Elsevier | por |
dc.rights | openAccess | por |
dc.subject | Pseudosaccharin | en |
dc.subject | 3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide | en |
dc.subject | Chapman rearrangement | en |
dc.subject | DFT calculation | en |
dc.subject | Infrared spectroscopy | en |
dc.subject | Thermomicroscopy | en |
dc.title | 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 | por |
dc.type | article | por |
degois.publication.firstPage | 3296 | por |
degois.publication.lastPage | 3305 | por |
degois.publication.title | Tetrahedron | por |
dc.peerreviewed | Yes | por |
dc.identifier.doi | 10.1016/j.tet.2008.02.007 | - |
degois.publication.volume | 64 | por |
uc.controloAutoridade | Sim | - |
item.fulltext | Com Texto completo | - |
item.grantfulltext | open | - |
item.languageiso639-1 | en | - |
item.cerifentitytype | Publications | - |
item.openairetype | article | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.researchunit | CQC - Coimbra Chemistry Centre | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.parentresearchunit | Faculty of Sciences and Technology | - |
crisitem.author.orcid | 0000-0002-8705-0160 | - |
crisitem.author.orcid | 0000-0002-5515-7721 | - |
crisitem.author.orcid | 0000-0002-8264-6854 | - |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais I&D CQC - Artigos em Revistas Internacionais |
Files in This Item:
File | Description | Size | Format | |
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Tetrahedron, 64 (2008) 3296.pdf | 1.17 MB | Adobe PDF | View/Open |
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