Sample records for benzopinacol

  1. Oxidation reactions with lead (IV) sulfonates and the preparation of potential antiradiation agents via thiirane 1,1-dioxides

    SciTech Connect

    Harmon, J.P.


    Lead tetraacetate (LTA) in the presence of sulfonic acids was studied in the hope of producing a more potent oxidant than LTA (owing to displacement of the weaker acetic acid by strong sulfonic acids). LTA in the presence of CF/sub 3/SO/sub 3/H (greater than or equal to4 equiv.) will cleave benzopinacol to benzophenone. LTA in the presence of CH/sub 3/SO/sub 3/H will methanesulfonoxylate diethyl malonate, methyl acetoacetate, and ethyl cyanoacetate. In the presence of CH/sub 3/SO/sub 3/H, MeOH, and CHCl/sub 3/, LTA will convert dialkyl and diaryl disulfides to methyl sulfinate esters. In a variation with Pb/sub 3/O/sub 4/, CH/sub 3/SO/sub 3/H, and P/sub 2/O/sub 5/ in ChCl/sub 3/, diethyl malonate was converted to a methanesulfonoxymalonate ester and to the monochloro-and dichloromalonates. Pb/sub 3/O/sub 4/, CH/sub 3/SO/sub 3/H, and P/sub 2/O/sub 5/ in benzene gave phenyl methanoesulfonate. A camphor 1,10-episulfone was prepared by the reaction of D-(+)-10-camphorsulfonyl chloride with Et/sub 3/N and CH/sub 2/N/sub 2/. The episulfone was cleaved at the least-hindered carbon atom using p-thiocresolate to give the corresponding ..beta..-substituted ethanesulfinate salt. Also, thiirane 1,1-dioxide, prepared from SO/sub 2/ and CH/sub 2/N/sub 2/, was cleaved with sodium phenylmethanethiolate and p-thiocresolate, Li/sub 3/SPO/sub 3/, Na/sub 2/S/sub 2/O/sub 3/, and sodium p-toluenethiosulfate to give the corresponding ..beta..-substituted ethanesulfinates.