Diinsertion of fluorenylidene into a Sulfur-Sulfur bond of diaryl disulfides

Article abstract of DOI:10.1016/S0040-4039(97)10402-6

Upon irradiation (>340 nm) of a benzene solution of diazofluorene with di-p-tolyl- or di-p-anisyl disulfide, the corresponding 9,9'-bis(arylmercapto)bifluorenyl was afforded in moderate to good yield accompanied by formation of 9,9'-bis(arylmercapto)fluorene. The major reaction pathway is considered to be a disulfur ylide formation followed by two times of successive Stevens rearrangement or by concerted electron redistribution via [2,3]sigmatropic rearrangement.