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

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.

Fil: Almeida, R.. Universidad de Coimbra; Portugal

Fil: Gomez Zavaglia, Andrea. Universidad de Coimbra; Portugal. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina

Fil: Kaczor, A.. Universidad de Coimbra; Portugal

Fil: Cristiano, M. L. S.. Universidad de Algarve; Portugal

Fil: Eusébio, M. E. S.. Universidad de Coimbra; Portugal

Fil: Maria, T. M. R.. Universidad de Coimbra; Portugal

Fil: Fausto, R.. Universidad de Coimbra; Portugal