Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/5023
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.
URI: http://hdl.handle.net/10316/5023
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

Files in This Item:
File Description SizeFormat
file0bcb09ba2f484e8d854429b93a52bfe7.pdf1.17 MBAdobe PDFView/Open
Show full item record

Page view(s) 50

284
checked on Oct 15, 2019

Download(s)

87
checked on Oct 15, 2019

Google ScholarTM

Check


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.