RHODIUM CARBENOID MEDIATED CYCLISATIONS. SYNTHESIS AND REARRANGEMENT OF CYCLIC SULPHONIUM YLIDES

Article abstract of DOI:10.1016/S0040-4039(00)82252-2

Treatment of diazo sulphides with rhodium (II) acetate in benzene gives six- and seven-membered cyclic sulphonium ylides; although the S-benzyl and S-ethyl ylides can be isolated, they rearrange, or eliminate ethylene respectively, on heating; the S-allyl ylides cannot be isolated since they undergo spontaneous <2,3>-sigmatropic rearrangement.