Helvetica Chimica Acta p. 549 - 553 (1991)
Update date:2022-08-10
Topics:
Langenbahn, Meinhard
Stoeckli-Evans, Helen
Suess-Fink, Georg
In the presence of catalytic amounts of [Ru2(CO) 4(Me2CNO)2(Me2CNOH)2](1), a cetone oxime reacts with carbon monoxide to give 2,3,4,5-tetrahydro-2,2,4,4, 6-pentamethylpyrimidine ('a cetonine'), CO2, and NH3. The reaction proceeds presumably via carbonylation of Me2C=NOH to the unstable intermediate Me2C=N-OCHO which undergoes decarboxylation to give the corresponding imine Me2C=NH. The final product is assumed to result from the cyclotrimerisation of Me2C=NH with elimination of NH3. Evidence for the intermediacy of the imine comes from the analogous reaction of acetophenone oxime, PhMeC=NOH, which gives the corresponding imine PhMeC=NH as a stable product. The isolation of the complex [RU2(CO)5(Me2CNO)2(Me 2CNOH)] (2) suggests the carbonylation to take place at the bridging oximato ligand of 1.
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