Journal of Organic Chemistry p. 4433 - 4438 (1981)
Update date:2022-08-05
Topics: Catalyzed Hydroformylation Experimental terms Bisolefinic Amine Derivatives Cobalt and Rhodium
Garst, Michael E.
Lukton, David
Three bisolefinic carbamates and five N,N-diallyl N-substituted amines have been subjected to hydroformylation conditions under catalysis by HCo(CO)4, Co(CO)8 and (Ph3P)3Rh(H)CO in an attempt to prepare heterocyclic ketones.The products differ with amines and carbamates and with catalyst.Carbamate 3 and HCo(CO)4 gave 3-pyrrolidinone (4) in 45percent yield.The cobalt-catalyzed reaction of 8 and rhodium-catalyzed reaction of 3 and of 8 afforded products arising from hydroformylation at the terminal olefinic carbon.These mixtures usually included 2-pyrrolidinone; cobalt-catalyzed hydroformylation of chlorinated allylamines 10-12 provided N-benzyl-2-pyrrolidinone (14) and N,N-dibutylbenzylamine (16).Direct synthesis of potential intermediates including 18 has permitted the delineation of mechanistic rationale.
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Doi:10.1016/S0040-4039(01)90493-9
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