The diastereoselective Michael addition of the title anion to alpha-hydrogen- and alpha-methyl-substituted conjugated nitroalkenes leads to new gamma-nitrocarbene complexes and gamma-hydroximoamides, respectively. The gamma-nitrocarbene complexes can be quantitatively oxidized to gamma-nitrobutyric acid derivatives (precursors of GABA derivatives); the gamma-hydroximoamides are formed as a result of an unexpected intramolecular transfer of an oxygen atom from the nitro group to the carbene atom, with elimination of the pentacarbonyl-chromium(0) group, which is recovered in high yield as the PyCr(CO)(5) complex
Licandro, E., Maiorana, S., Capella, L., Manzotti, R., Papagni, A., Pryce, M., et al. (1998). The anion of the pentacarbonyl[(trans-2,6-dimethylmorpholino)-(methyl)carbene]chromium complex in the reactions with nitroalkenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(10), 2127-2133 [10.1002/(SICI)1099-0690(199810)1998:10<2127::AID-EJOC2127>3.0.CO;2-U].
The anion of the pentacarbonyl[(trans-2,6-dimethylmorpholino)-(methyl)carbene]chromium complex in the reactions with nitroalkenes
Papagni, A;
1998
Abstract
The diastereoselective Michael addition of the title anion to alpha-hydrogen- and alpha-methyl-substituted conjugated nitroalkenes leads to new gamma-nitrocarbene complexes and gamma-hydroximoamides, respectively. The gamma-nitrocarbene complexes can be quantitatively oxidized to gamma-nitrobutyric acid derivatives (precursors of GABA derivatives); the gamma-hydroximoamides are formed as a result of an unexpected intramolecular transfer of an oxygen atom from the nitro group to the carbene atom, with elimination of the pentacarbonyl-chromium(0) group, which is recovered in high yield as the PyCr(CO)(5) complex
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