Rhodium- catalysed reactions of o- or p- cyano-N-allylanilines with H2/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 H2/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-{1-(2-cyanophenyl)-3-methylpyrrolidin-2-yl}-1,2,3,4-tetrahydropyridin-1-yl] benzonitrile ) was confirmed by an X-ray single-crystal structure determination.
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Rhodium- catalysed hydroformylation of readily available ortho-propenylanilines gives 4,5- dihydro-3H-1-benzazepines together with small amounts of substituted 3-methylquinolines (≤15%). The regioselectivity of these reactions and the hydroformylation of related ortho-propenylphenols are discussed.
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