INVESTIGADORES
PELLEGRINET Silvina Carla
artículos
Título:
The Dienone-Phenol Rearrangement of Santonin: A Comprehensive Laboratory Experiment for Advanced Undergraduate Organic Chemistry Students
Autor/es:
MARÍA I. COLOMBO; SEBASTIÁN TESTERO; SILVINA C. PELLEGRINET; MARÍA L. BOHN; EDMUNDO A. RÚVEDA
Revista:
The Chemical Educator
Editorial:
Springer-Verlag New York, Inc.
Referencias:
Año: 2001 vol. 6 p. 350 - 352
ISSN:
1430-4171
Resumen:
A comprehensive laboratory experiment suitable for advanced undergraduate organic chemistry students has been designed. The experiment is based on the dienone.phenol rearrangement reaction of the sesquiterpene santonin to give á-desmotroposantonin acetate. It challenges students to solve an earlier controversial stereochemical problem. The students carry out the reaction and analyze spectroscopic data to determine the stereochemistry of the starting material and the product. In addition, they perform simple molecular modeling calculations, which enable them to rationalize the stereochemical outcome of the transformation and discuss the mechanism of the dienone.phenol rearrangement and related rearrangements reported in the literature.
