Reactions of unsaturated amides under hydroformylation conditions

Article abstract of DOI:10.1016/0022-328X(90)80010-W

N,N-diethyl methacrylamide (1) undergoes hydroformylation, followed by subsequent reactions, under "oxo" conditions involving use of Rh4(CO)12 or Rh4(CO)12 in the presence of (R,R)-Diop (Diop = <2,2-dimethyl-1,3-dioxolane-4,5-diylbis (methylene)bis(diphenylphosphine)) as the catalyst precursor.The product first formed arises from formylation at the unsubstituted unsaturated carbon atom, and subsequently gives α-methyl-γ-butyrolactone (1b), N,N-diethyl 2-methyl-4-hydroxy-butyramide (1e), and N, N-diethyl 1-methyl-3-(diethylamino)butyramide (1f).Hydrogenation of the substrate takes also place.The product distribution can be strongly influenced by the reactions conditions.For N,N,N',N'-tetraethyl itacondiamide (2) under similar reactions conditions only hydrogenation and isomerization products are formed.