1227261-83-7Relevant academic research and scientific papers
New methodology for the conversion of epoxides to alkenes
Wu, Feng-Ling,Ross, Benjamin P.,McGeary, Ross P.
, p. 1989 - 1998 (2010)
Epoxides have been transformed in good yields to alkenes by a process involving (i) ring-opening of the epoxide with 2-mercaptobenzothiazole, (ii) oxidation of the derived ss-hydroxy thioethers to the corresponding sulfones, and (iii) thermal or base-promoted fragmentation of these sulfones to alkenes. The stereochemistry of the starting epoxide is transfer-red faithfully to the alkene product, because of the SN2 epoxide ring-opening reactions and the antiperiplanar SO2 elimination reaction of the ss- alkoxysulfinate intermediates. This methodology may form the basis of a new protecting group strategy for alkenes.
