Intramolecular rearrangement of thioozonides: Sulfine formation without sulfur atom scrambling,a double isotope crossover study |
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| Affiliation: | 1. Centro de Investigaciones Biológicas (C.S.I.C), c/ Ramiro de Maeztu 9, 28040, Madrid, Spain;2. Instituto de Biología, Pontificia Universidad Católica de Valparaíso, Avenida Universidad 330, Campus Curauma, Curauma, Valparaíso, Chile;1. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, PR China;2. Netherlands Centre for Biodiversity Naturalis, PO Box 9517, 2300 RA Leiden, The Netherlands;3. Institute für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb.26.23, 40225 Düsseldorf, Germany;1. Department of Pharmaceutical Sciences, School of Pharmacy, University of Puerto Rico, Medical Sciences Campus, San Juan, PR 00936, USA;2. School of Pharmacy, Faculty of Medical Sciences, The University of the West Indies, St. Augustine, Trinidad and Tobago, West Indies;1. State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences, Guangzhou 510640, China;2. Department of Chemistry and Biochemistry, Old Dominion University, Norfolk, VA 23529, USA |
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| Abstract: | Decomposition of a mixture of 34S and deuterium labeled thioozonides prepared by photooxidation of dimethylthiophenes in CDCl3 has shown that intramolecular rearrangement to thioketone S-oxide, a stable 1,3-dipole, proceeds cleanly without sulfur atom scrambling in the presence of sulfur allotropes. |
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