Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.1/4257
Título: 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
Autor: Almeida, R.
Gómez-Zavaglia, A.
Kaczor, A.
Cristiano, Maria Lurdes Santos
Eusébio, M. E. S.
Maria, T. M. R.
Fausto, R.
Palavras-chave: Pseudosaccharin
Chapman rearrangement
DFT calculations
Infrared spectroscopy
DSC
Thermomicroscopy
3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide
Data: 2008
Editora: Elsevier
Citação: Almeida, 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.
Resumo: 3-(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.
Peer review: yes
URI: http://hdl.handle.net/10400.1/4257
DOI: http://dx.doi.org/10.1016/j.tet.2008.02.007
ISSN: 0040-4020
Aparece nas colecções:CCM2-Artigos (em revistas ou actas indexadas)



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