Microwave-Induced Synthesis of a Cis–Trans Mixture of 2-Butyl-5-phenyl-1,3-dioxolan-4-ones and Their Stereochemical Determination Using NOESY 2-D NMR Spectroscopy

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 8 Issue 1 (2003) pp 33-36

Microwave-Induced Synthesis of a Cis–Trans Mixture of 2-Butyl-5-phenyl-1,3-dioxolan-4-ones and Their Stereochemical Determination Using NOESY 2-D NMR Spectroscopy

Timothy L. Friebe

Department of Chemistry, Eastern Michigan University, Ypsilanti, MI 48197, tfriebe@online.emich.edu
Received November 11, 2002. Accepted December 7, 2002

Published online: 15 January 2003

Abstract. We report a new organic laboratory experiment designed for the undergraduate/advanced undergraduate student. In this experiment, students first model the two possible diastereomeric (cis–trans) dioxolanone products, predict the major isomer, and then go into the laboratory and rapidly synthesize the diastereomeric mixture using a domestic microwave oven as a heat source. Finally, the stereochemistry of the major isomer is confirmed using NOESY 2-D NMR spectroscopy.

Key Words: Laboratories and Demonstrations; organic chemistry; synthesis; NMR

(*) Corresponding author. (E-mail: tfriebe@online.emich.edu)

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