Allylation alkane carbon-sulfur bond

Catalytic hydrogenation is mostly used to convert C—C triple bonds into C C double bonds and alkenes into alkanes or to replace allylic or benzylic hetero atoms by hydrogen (H. Kropf, 1980). Simple theory postulates cis- or syn-addition of hydrogen to the C—C triple or double bond with heterogeneous (R. L. Augustine, 1965, 1968, 1976 P. N. Rylander, 1979) and homogeneous (A. J. Birch, 1976) catalysts. Sulfur functions can be removed with reducing metals, e. g. with Raney nickel (G. R. Pettit, 1962 A). Heteroaromatic systems may be reduced with the aid of ruthenium on carbon. 

Sulfur compounds. Displacement of allylic carbonates with thiols takes place at room temperature. Linear products also predominate from reaction with secondary carbonates. l,2-Bis(phenylthio)alkanes are formed when 1-alkenes are treated with diphenyl disulfide under catalytic conditions ([Ru] catalyst, toluene, 100°). Various functional groups (ester, silyl, etc.) directly bonded to the double bond are tolerated. 

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See also in sourсe #XX -- [ , ]

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