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Title: Thermally Induced Sigmatropic Isomerization of Pseudosaccharyl Allylic Ether
Authors: Gómez-Zavaglia, A. 
Kaczor, A. 
Almeida, R. 
Cristiano, M. L. S. 
Eusébio, M. E. S. 
Maria, T. M. R. 
Mobili, P. 
Fausto, R. 
Issue Date: 16-Apr-2009
Publisher: American Chemical Society
Citation: The Journal of Physical Chemistry A. 113:15 (2009) 3517-3522
Abstract: The thermally induced sigmatropic isomerization of the pseudosaccharyl allylic ether [3-(allyloxy)-1,2-benzisothiazole 1,1-dioxide; ABID] has been investigated by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry, and polarized light thermomicroscopy, complemented by theoretical methods. Migration of the allylic system from O to N occurs in the melted ABID, and the thermally obtained 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) starts to be produced at ca. 150 °C, in a process with an activation energy of 92 kJ mol−1. From kinetic data, a concerted [3,3′] sigmatropic mechanism is proposed. In the temperature range investigated, ABIOD was found to exhibit polymorphism. Cooling of the molten compound leads to the production of a metastable crystalline form, which upon annealing at room temperature might be transformed to the stable crystalline phase. ABID shows a single crystalline variety. Assignments were proposed for the infrared spectra of the observed neat condensed phases of the two compounds.
ISSN: 1089-5639
DOI: 10.1021/jp8112254
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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