First observation of Chapman rearrangement of a pseudosaccharin ether in the solid-state: the thermal rearrangement of 3-(methoxy)-1,2-benzisothiazole 1,1-dioxide revisited

R. ALMEIDA, A. GÓMEZ-ZAVAGLIA, A. KACZOR, M.L.S. CRISTIANO, M.E.S. EUSÉBIO, T.M.R. MARIA, R. FAUSTO

TETRAHEDRON

Elsevier

Lugar: Amsterdam; Año: 2008 vol. 64 p. 3296 - 3305

0040-4020

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.