Journal of Organic Chemistry p. 3303 - 3307 (1987)
Update date:2022-08-05
Topics:
Baldwin, John E.
Barden, Timothy C.
Pugh, Ruth L.
Widdison, Wayne C.
Decarbonylations of trans-2-phenylcyclopropanedeuteriocarboxaldehyde and cycloheptanedeuteriocarboxaldehyde with Wilkinson's catalyst give phenylcyclopropane and cycloheptane with partial loss of deuterium label.Loss of deuterium label is not a consequence of orthometalation of deuteriotris(triphenylphosphine)rhodium(I), a plausible reactive intermediate, for the loss is observed even when RhCl(P(C6D5)3)3 is used to effect the decarbonylation.Decarbonylations of trans-2-phenylcyclopropanecarboxaldehyde with Wilkinson's catalyst in benzene containing O-deuterioethanolafford d0 and d1 phenylcyclopropane and d0 and d1 aldehyde; neither hydrocarbon product nor recovered aldehyde is deuterium labeled when 1,1-dideuterioethanol is present in the decarbonylation reaction mixture.The hydroxyl hydrogen of ethanol associated with RhCl(P(C6H5)3)3 as normally synthesized, however, is not the hydrogen source: ethanol is not detected by 1H NMR in solutions of the catalyst, loss of deuterium label occurs even when RhCl(PPh3)3 is prepared free of possible contamination by ethanol from
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