Stable Dicarbonylcarbene Complexes of Bis(oxazolinyl)pyridine Ruthenium and Osmium

The reaction of RuCl2(pybox)(C2H4) [pybox = 2,6-bis(oxazolinyl)pyridine] 1 and OsCl2(pybox)(propylene) 6 with dimethyl diazomalonate gave stable dicarbonylcarbene complexes 9 and 10 in 92% and 59% yields, respectively. The carbene moiety of 9 proved to be almost parallel in the Cl-Ru-Cl plane ny 10–12° and perpendicular to the pybox plane by X-ray analysis. The transfer of the carbene moiety of 9 to styrene could be observed at 110 °C to give the corresponding cyclopropane 15 but in a low yield (11%) with asymmetric induction in 36% ee.