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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 | Authors: | Almeida, R. Gómez-Zavaglia, A. Kaczor, A. Cristiano, M. L. S. Eusébio, M. E. S. Maria, T. M. R. Fausto, R. |
Keywords: | Pseudosaccharin; 3-(Methoxy)-1,2-benzisothiazole 1,1-dioxide; Chapman rearrangement; DFT calculation; Infrared spectroscopy; Thermomicroscopy | Issue Date: | Apr-2008 | Publisher: | Elsevier | Serial title, monograph or event: | Tetrahedron | Volume: | 64 | 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 | URI: | https://hdl.handle.net/10316/17941 | DOI: | 10.1016/j.tet.2008.02.007 | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais I&D CQC - Artigos em Revistas Internacionais |
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Tetrahedron, 64 (2008) 3296.pdf | 1.17 MB | Adobe PDF | View/Open |
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