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Microscale Synthesis of a Diphenylisoxazoline by a 1,3-Dipolar Cycloaddition

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William B. Martin , Laura J. Kateley , Dawn C. Wiser and Catherine A. Brummond

Department of Chemistry, Lake Forest College, Lake Forest, IL 60045-2399

J. Chem. Educ., 2002, 79 (2), p 225

DOI: 10.1021/ed079p225

Publication Date (Web): February 1, 2002

Section:

History, Education, and Documentation

Abstract

This microscale synthesis of a diphenylisoxazoline gives students an opportunity to prepare and examine the heterocyclic product of a pericyclic 1,3-dipolar addition reaction analogous to a Diels-Alder reaction. Two reaction pathways are proposed, one leading to 3,4-diphenylisoxazoline and the other to 3,5-diphenylisoxazoline. The ¹H NMR spectrum of the actual product is used to determine its structure and thus the reaction pathway. The proposed products have diasteriotopic hydrogens that are readily observed in the ¹H NMR spectra. Molecular modeling also is used to predict which product is more probable and to offer a likely explanation for the regioselectivity of the reaction.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Microscale Lab

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