Evidence for Equilibrium between N -Substituted 3-Phosphorylidenepyrrolidine-2,5-diones and N -Substituted Maleimides and Phosphines: Thermal Instability of the N -Substituted Phosphoranes
Free accessResearch articleFirst published online December, 1999
Evidence for Equilibrium between N -Substituted 3-Phosphorylidenepyrrolidine-2,5-diones and N -Substituted Maleimides and Phosphines: Thermal Instability of the N -Substituted Phosphoranes
The formation of N-substituted 3-phosphorylidenepyrrolidine-2,5-diones from N-substituted maleimides and phosphines is reversible and at elevated temperature the phosphoranes behave as a source of maleimide derivatives which give the corresponding cycloadducts with nitrones and 1,3-dienes; a consequence of this equilibrium is the thermal instability of the ylides.
References
1.
BlackD. St. C. and DavisV. C., Aust. J. Chem., 1976, 29, 1735.
2.
HedayaE. and TheodoropulosS., Tetrahedron, 1968, 24, 2241.
3.
Koszytkowska-StawinskaM., SasW. and SowinskaA., J. Chem. Res. (S), 1996, 162.
4.
Koszytkowska-StawinskaM. and SasW., J. Chem. Res.1998, (S) 298; (M) 1356.
5.
HodgeP., KhoshdelE. and NairnA. A., Polym. Commun., 1986, 27, 322.
6.
BarrettA. G. M., BroughtonH. B., AttwoodS. V. and GunatilakaA. A. L, J. Org. Chem., 1986, 51, 495.
