Regioselective And Stereoselective Cleavages Of P-S/C-S Bonds By Lithium And The Formation Of P-Stereogenic Functional Phosphine Derivatives

Various menthyl-containing phosphinothioates were prepared. Using these compounds, an unusual phosphorus-promoted cleavage of the C-S bond with lithium-naphthalene was examined. The C-S/P-S cleavages could be controlled by the amount of naphthalene and temperature applied. Also, the P-S cleavage was confirmed to retain the configuration about the P and this feature was used for achieving a stereospecific formation of the C-P bond.