ISSN:
0947-3440
Keywords:
Sulfines
;
Structure elucidation
;
Conformation analysis
;
Rearrangements
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The structure of dimesityl sulfine in solution and in the solid state was determined by NMR spectroscopy and X-ray crystallography, respectively. In the crystal the two mesityl groups are twisted by approximately 60°, while in solution an averaged conformation with Cs symmetry is observed, with the anti mesityl ring located in the C=S=O plane and the syn mesityl ring perpendicular to the C=S=O plane. From the coalescence temperature Tc at 303 K, the free energy of activation for the rotation of the mesityl rings was estimated to be 14 ± 0.7 kcal/mol. At higher temperatures (140-185°C) dimesityl sulfine yields up to 95% 5,7-dimethyl-1-mesityl-benzo[c]thiophene.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719971214
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