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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, Andrea 
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 calculations; Infrared spectroscopy; Thermomicroscopy
Issue Date: 2008
Citation: Tetrahedron. 64:15 (2008) 3296-3305
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.
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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