Cyclization of 1,3-diaryl-3-phenylsulfanyl-1-propanols to thiochromans with the participation of [1,3]-PhS shift |
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| Authors: | Jacek Skar?ewski Mariola Zielińska-B?ajetSzczepan Roszak Ilona Turowska-Tyrk |
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| Institution: | a Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroc?aw University of Technology, Wybrzeze S. Wyspianskiego, 50-370 Wroc?aw, Poland
b Institute of Physical and Theoretical Chemistry, Wroc?aw University of Technology, 50-370 Wroc?aw, Poland |
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| Abstract: | Optically active (3R,1RS)-3-aryl-1-phenyl-3-phenylsulfanyl-1-propanols were easily dehydrated forming mainly rac-cis-2-aryl-4-phenylthiochroman, and rac-cis-4-aryl-2-phenylthiochroman along with the corresponding trans-isomers. The observed reaction outcome (rearrangement and racemisation) apparently results from the SEAr reaction involving the unusual 1,3-phenylsulfanyl group migration. This interpretation is supported by the results of theoretical studies (DFT) on the supposed intermediates. |
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| Keywords: | cyclization thiochromans [1 3]-sulfanyl participation X-ray structures DFT calculations |
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