The dimerization and photochemical rearrangement of pentacyclo-[5.4.0.0.0.0]undecane-8-thione |
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| Authors: | Colin E Read Frans JC Martins Agatha M Viljoen |
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| Institution: | School of Chemistry and Biochemistry, North-West University, Potchefstroom 2520, South Africa |
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| Abstract: | Pentacyclo5.4.0.02,6.03,10.05,9]undecan-8-one 1 is readily sulfurated into pentacyclo5.4.0.02,6.03,10.05,9]undecane-8-thione 2 with Lawesson’s reagent in dry THF. Upon standing at ambient temperature the thione 2 formed the corresponding thio-dimer 3 within 10 days. When the thio-dimer 3 was exposed to oxygen and ultraviolet light an unexpected photochemical oxidation and rearrangement took place to form the stable disulfenate 5. |
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| Keywords: | Pentacyclo[5 4 0 02 6 03 10 05 9]undecane-8-thione Disulfenate Disulfoxide Lawesson&rsquo s reagent Photochemical rearrangement |
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