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