Tetrahedron Letters p. 201 - 204 (1995)
Update date:2022-08-17
Topics:
Abu-Yousef, Imad A.
Harpp, David N.
When triphenylmethanesulfenyl chloride (8) (or its thio 9 and dithio 10 homolog) is treated with adamantylideneadamantane (11), adamantylideneadamantn thiirane (12) is produced (92%). Compound 12 was treated with m-chloroperoxybenzoic acid (m-CPBA) forming adamantylideneadamantane thiirane 1-oxide (13) in 99% isolated yield. The structures of 12 and 13 were established by 1H and 13C NMR, mass spectrometry as well as by X-ray analysis. Sulfoxide 13 decomposes smoothly to deliver sulfur monoxide in good yield to various dienes.
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