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■ A Novel Approach to 5,5’-Diisopropyl-3,3’-bi-2H-cyclohepta[b]furan-2-one

Noboru Morita,* Junya Higashi, Kazuyuki Okada, Taku Shoji, Kozo Toyota, Masataka Watanabe, Masafumi Yasunami, Shigeru Kikuchi, and Shunji Ito

*Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan

Abstract

5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b]furan-3-yl)sulfonium trifluoromethanesulfonate (2), which was treated with Et₃N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf₂O converted to an unexpected product, 5,5’-diisopropyl-3,3’-bi-2H-cyclohepta[b]furan-2-one (7), thermally.