Almeida, R.Gómez-Zavaglia, A.Kaczor, A.Cristiano, Maria Lurdes SantosEusébio, M. E. S.Maria, T. M. R.Fausto, R.2014-06-092014-06-092008Almeida, 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, 2008.0040-4020AUT: MCR00716;http://hdl.handle.net/10400.1/42573-(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.engPseudosaccharinChapman rearrangementDFT calculationsInfrared spectroscopyDSCThermomicroscopy3-(Methoxy)-1,2-benzisothiazole 1,1-dioxidejournal article2014-06-05http://dx.doi.org/10.1016/j.tet.2008.02.007