A USEFUL PRECURSOR FOR SULFUR MONOXIDE TRANSFER

When triphenylmethanesulfenyl chloride (8) (or its thio 9 and dithio 1 0 homolog) is treated with adamantylideneadamantane (11), adamantylide neadamantane thiirane (12) is produced (92%). Compound 12 was treated with m-chloroperoxybenzoic acid (m-CPBA) forming adamantylideneadamant ane thiirane 1-oxide (13) in 99% isolated yield. The structures of 12 and 13 were established by H-1 and C-13 NMR, mass spectrometry as well as by X-ray analysis. Sulfoxide 13 decomposes smoothly to deliver sul fur monoxide in good yield to various dienes.