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2H-Cyclohepta[b]furan-2-ones (2a,b) reacted with dimethyl sulfide dittiflate to give dimethyl(2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonates (3a,b), which were treated with Et 3 N to give 3-methylthio-2H-cyclohepta[b]furan-2-ones (4a,b). Sulfides 4a and 4b were oxidized with m-CPBA to give corresponding sulfoxides (5a,b) and sulfones (6a,b). The sulfoxides (5a,b) thermally underwent coupling reaction to give 3,3'-bi-2H-cyclohepta[b]furan-2-ones (7a,b). The sulfoxides (5a,b) reacted with trifluoromethanesulfonic anhydride (Tf 2 O) to afford sulfonium ions 8a and 8b at lower temperature, which reacted with 2a or 2b to give sulfonium ions (9a-c). Treatment of compounds 9a-c with Et 2 NH or Et 3 N gave corresponding sulfide products (10a-c).

Synthesis and Reactivity of 3-Methylsulfinyl-2H-cyclohepta[b]furan-2-ones