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The Chemical Educator
ISSN: 1430-4171 (electronic version)
Abstract Volume 6
Issue 6 (2001) pp 350-352
The Dienone–Phenol Rearrangement of Santonin: A Comprehensive Laboratory Experiment for Advanced Undergraduate Organic Chemistry Students
María I. Colombo, Sebastián A. Testero, Silvina C. Pellegrinet, María L. Bohn and Edmundo A. Rúveda*
Instituto de Química Orgánica y de Síntesis (CONICET-UNR),
Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla
de Correo 991, 2000 Rosario, Argentina
Received March 28, 2001. Accepted July 17, 2001
Published online: 12 October 2001
Abstract. 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 a-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.
Key Words: Laboratories and Demonstrations; organic chemistry; synthesis; stereochemical; computational; modeling
(*) Corresponding author. (E-mail: eruveda@fbioyf.unr.edu.ar)
Article in PDF format (137 KB) HTML format
Supporting Materials:
Student Handout (151 KB) 10.1007/s00897010511b.
Issue date: December 7, 2001
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