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Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid

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Steven C. Cermak and David F. Wiemer

Department of Chemistry, University of Iowa, Iowa City, IA 52242

J. Chem. Educ., 1999, 76 (12), p 1715

DOI: 10.1021/ed076p1715

Publication Date (Web): December 1, 1999

Section:

History, Education, and Documentation

Abstract

The preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments. The absolute configuration remains the same through this series of transformations, but the sign of the optical rotation is reversed from the sulfonamide to the sulfonylimine, and again from the sulfonylimine to the oxaziridine. The latter two intermediates are readily purified by crystallization, and their optical rotations are easily measured.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Stereochemistry

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