1,3-Dipolar Activity in Cycloadditions of an Aliphatic Sulfine(,)(1).
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.
Huisgen
Rolf
R
Institut für Organische Chemie der Universität München, Karlstrasse 23, D-80333 München, Germany.
Mloston
Grzegorz
G
Polborn
Kurt
K