Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/17941
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. 
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: http://hdl.handle.net/10316/17941
DOI: 10.1016/j.tet.2008.02.007
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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