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New insight into chiroptical properties of 1,2-diols cyclic sulfites.

Authors
Type
Published Article
Journal
The Journal of Organic Chemistry
1520-6904
Publisher
American Chemical Society
Publication Date
Volume
74
Issue
19
Pages
7300–7308
Identifiers
DOI: 10.1021/jo9012964
PMID: 19715285
Source
Medline
License
Unknown

Abstract

The present work examines the relationship between the structure and chiroptical properties of cyclic sulfites utilizing the electronic circular dichroism (CD) and time-dependent density functional theory (TD-DFT). For some of the model compounds the study was additionally supported by the X-ray diffraction analysis. A comparison of the experimental and simulated CD spectra gave a reasonable interpretation of the Cotton effects observed in the 200-220 nm spectral range. The study revealed a high sensitivity of the CD spectra with regard to the configuration at the sulfur atom as well as the conformation of the ring bearing the sulfite chromophore. The results demonstrated that such a combined treatment enabled the determination of absolute configuration with a high degree of confidence.

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