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An α,α‘-Dioxothione and Its [4 + 2] Cycloaddition with trans-Cyclooctene in the Reaction of Ninhydrin with Potassium Thiotosylate

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journal contribution
posted on 08.07.2000, 00:00 by Waldemar Adam, Bettina Fröhling
In the reaction of Ninhydrin (1a)/1,2,3-indantrione (1b) with potassium thiotosylate, 1,4-oxathiin 6 is formed in up to 63% yield as the trapping product of the intermediary α,α‘-dioxothione 1c with trans-cyclooctene (3a). Additionally, up to 18% of the available sulfur is transferred to olefin 3a to thiirane 3b through the intermediary oxathiirane.