Direct episulfidation of alkenes and allenes with elemental sulfur and thiiranes as sulfur sources,catalyzed by molybdenum oxo complexes |
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Authors: | Adam Waldemar Bargon Rainer M Schenk Wolfdieter A |
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Institution: | Contribution from the Institut für Organische and Anorganische Chemie der Universit?t Würzburg, Am Hubland, Germany. adam@chemie.uni-wuerzburg.de |
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Abstract: | The molybdenum oxo complexes 1a and 1b catalyze efficiently the sulfur transfer to a series of alkenes 4 and allenes 6, for which elemental sulfur, phenylthiirane, or methylthiirane have been employed as sulfur sources to afford the corresponding episulfides 5 and 7. The most effective catalytic episulfidation system to date is the combination of the dithiophosphate-ligated oxo complex 1b and phenylthiirane (Ibeta). This metathesis process is efficient enough to convert usually reluctant alkenes (cyclopentene, cycloheptene, Z-cyclooctene, Z-cyclononene, E-cyclodecene, norbornene, and even bicyclopropylidene) to their episulfides in good yields under mild conditions. The direct catalytic sulfuration of allenes (cyclonona-1,2-diene, cyclonona-1,2,5-triene, cyclodeca-1,2-diene, and 2,4-dimethylpenta-2,3-diene) to their labile methylenethiiranes is unprecedented. |
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