The diastereoselective Michael addition of the title anion to α-hydrogen- and α-methyl-substituted conjugated nitroalkenes leads to new γ-nitrocarbene complexes and γ-hydroximoamides, respectively. The γ-nitrocarbene complexes can be quantitatively oxidized to γ-nitrobutyric acid derivatives (precursors of GABA derivatives); the γ-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 pentacarbonylchromium(0) group, which is recovered in high yield as the PyCr(CO)5 complex.
The anion of the pentacarbonyl[(trans-2,6-dimethylmorpholino)-(methyl)carbene]chromium complex in the reactions with nitroalkenes / Licandro, E.; Maiorana, S.; Capella, L.; Manzotti, R.; Papagni, A.; Pryce, M.; Graiff, C.; Tiripicchio, A.. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 10(1998), pp. 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
Graiff C.;Tiripicchio A.
1998-01-01
Abstract
The diastereoselective Michael addition of the title anion to α-hydrogen- and α-methyl-substituted conjugated nitroalkenes leads to new γ-nitrocarbene complexes and γ-hydroximoamides, respectively. The γ-nitrocarbene complexes can be quantitatively oxidized to γ-nitrobutyric acid derivatives (precursors of GABA derivatives); the γ-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 pentacarbonylchromium(0) group, which is recovered in high yield as the PyCr(CO)5 complex.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
