THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .60. RHODIUM-CATALYZED REACTIONS OF HYDROGEN AND CARBON-MONOXIDE WITH ALKENYLANILINES

Rhodium-catalysed reactions of o- or p-cyano-N-allylanilines with H-2/CO give N-arylpyrrolidine aldehydes resulting from a double hydroformylation sequence. In contrast reactions of o- or p-methyl-N-allylanilines or N-allylaniline itself with H-2/CO give 'dimeric' compounds resulting from self-condensation reactions of an initially formed hydroformylation product together with varying amounts of the double hydroformylation product. Similar reactions of o-cyano-N-but-3-enylanilines give low yields of double hydroformylation products and major products arising from hydrogenation or cross coupling of intermediate enamines. The structure of one of these products, N-2-cyanophenyl-5-(N'-2-cyanophenyl-3-methyl-pyrrolidin-2-yl)-1,2,3,4-tetrahydropyridine (17) (IUPAC name: 2-[5-fl-(2-cyanophenyl)-3-methylpyrrolidin-2-yl}-1,2,3,4-tetrahydropyridin-1-yl]benzonitrile) was confirmed by an X-ray single-crystal structure determination.