STEREOSELECTIVE SYNTHESIS OF 2,2-DISUBSTITUTED 1-FLUORO-ALKENES: (E)-[[FLUORO(2-PHENYLCYCLOHEXYLIDENE)-METHYL]SULFONYL]BENZENE AND (Z)-[2-(FLUOROMETHYLENE)-CYCLOHEXYL]BENZENE

Stereoselective synthesis of 2,2-disubstituted 1-fluoro-alkenes: (E)-[[fluoro(2-phenylcyclohexylidene)-methyl]sulfonyl]benzene and (Z)-[2-(fluoromethylene)-cyclohexyl]benzene product: (E)-[[Fluoro(2-phenylcyclohexylidene)methyl]sulfonyl]benzene (1) reactant: diethyl chlorophosphate (24.8 g, 0.14 mol) intermediate: (E)-Tributyl[fluoro(2-phenylcyclohexylidene)methyl]stannane (2) product: (Z)-[2-(Fluoromethylene)cyclohexyl]benzene (3) Keywords: condensation, carbonyl-ylide condensation; hydrolysis, miscellaneous; metalation reactions, lithium; metalation reactions, tin; phosphonation; replacement reactions, miscellaneous; stereoselective reactions, diastereoselective; benzene; diethyl chlorophosphate, highly toxic