SN2'Substitutions of 1,3-Dichloropropenes with the Functionalized Copper-Zinc Reagents RCu(CN)ZnX

Article abstract of DOI:10.1016/S0040-4039(00)98797-5

The addition of benzenesulfenyl (or benzeneselenyl) chlorides to propargylic chlorides affords regio- and stereospecifically (E)-1,3-dichloro-2-phenylsulfenyl (or phenylselenyl) propenes (2a-c).These new reagents were found to react with excellent S_N2'selectivity with the highly functionalized copper-zinc reagents RCu(CN)ZnX, affording polyfunctional vinylic-thioethers or -selenides of type 3.The acidic hydrolysis of 3 furnishes symmetrical ketones in good yields.