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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
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.
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Reference£º
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com