Abstract
2,2,4,4-Tetramethyl-3-thioxocyclobutanone S-oxide (4) combines with diaryl thioketones at room temperature furnishing spiro-1,2,4-oxadithiolanes 6 in equilibrium reactions. Compound 6a was oxidized to the cis-S,S-dioxide 9, the structure of which was established by X-ray analysis. These are the first unequivocal 1,3-cycloadditions of thione S-oxides (sulfines) which possess an allyl anion type MO; cycloadditions to the C=S bond of sulfines as dipolarophile and dienophile had been described before.
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