Journal article
Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid
Journal of chemical education, Vol.76(12), pp.1715-1716
12/1999
DOI: 10.1021/ed076p1715
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.
Details
- Title: Subtitle
- Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid
- Creators
- Steven C Cermak - Department of Chemistry, University of Iowa, Iowa City, IA 52242David F Wiemer - Department of Chemistry, University of Iowa, Iowa City, IA 52242
- Resource Type
- Journal article
- Publication Details
- Journal of chemical education, Vol.76(12), pp.1715-1716
- DOI
- 10.1021/ed076p1715
- ISSN
- 0021-9584
- eISSN
- 1938-1328
- Language
- English
- Date published
- 12/1999
- Academic Unit
- Neuroscience and Pharmacology; Chemistry
- Record Identifier
- 9984216720702771
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