Evidence for Equilibrium between N-Substituted 3-Phosphorylidenepyrrolidine-2,5-diones and N-Substituted Maleimides and Phosphines: Thermal Instability of the N-Substituted Phosphoranes

Abstract

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. D. St. C. Black and V. C. Davis, Aust. J. Chem., 1976, 29, 1735.
2. E. Hedaya and S. Theodoropulos, Tetrahedron, 1968, 24, 2241.
3. M. Koszytkowska-Stawinska, W. Sas and A. Sowinska, J. Chem. Res. (S), 1996, 162.
4. M. Koszytkowska-Stawińska and W. Sas, J. Chem. Res., 1998, (S) 298; (M) 1356.
5. P. Hodge, E. Khoshdel and A. A. Naim, Polym. Commun., 1986, 27, 322.
6. A. G. M. Barrett, H. B. Broughton, S. V. Attwood and A. A. L. Gunatilaka, J. Org. Chem., 1986, 51, 495.