Reaction of orthometallated perfluorocumyl alkoxides with sulfinyl derivatives: Synthetic and mechanistic aspects

the reaction of 1,1,1,3,3,3-hexafluoro-2-(p-tert-butyl)phenyl-2-propanol with n-butyl-lithium vertical bar N,N,N',N'-tetramethylethylenediamine (TMEDA) provides dilithio-derivative 1b, which upon reaction with thionyl chloride, gave cyclic and acyclic sulfites 3 and 4 as precursors of the sulfurane 2b with simultaneous formation of cyclic sulfinate 5. This ester was utilized for the preparation of asymmetrical spiro-sulfuranes 7 or ortho-perfluoroeumylaryl-(alkyl) sulfoxides 8. Attempts to obtain it as an optically active species are also mentioned.