A useful precursor for sulfur monoxide transfer

Article abstract of DOI:10.1016/0040-4039(94)02247-9

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.