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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > December  >
In the Laboratory
Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid
Steven C. Cermak and David F. Wiemer
Department of Chemistry, University of Iowa, Iowa City, IA 52242
Cover
December 1999
Vol. 76 No. 12
p. 1715
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.
Supplement
Experimental procedures and a chemicals list are provided.
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*  Citation
 Cermak, Steven C.; Wiemer, David F. J. Chem. Educ. 1999 76 1715.
*  Keywords
 Organic Chemistry; Stereochemistry; Laboratory Instruction; Organic Synthesis
*  History
 Created:
Last Updated:		 November 10, 1999
November 22, 2005
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