Regioselectivity in nucleophilic ring-opening of aziridinones

Chemical Communications

Volumn , Issue 9, 1998, Pages 985-986

  Talaty, Erach R ^a   Yusoff, Mashitah M ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002901991     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a800564h     Document Type: Article

References (12)

1. I. Lengyel and J. C. Sheehan, Angew. Chem., Int. Ed. Engl., 1968, 25.
2. G. L'abbe, Angew. Chem., Int. Ed. Engl., 1980, 276.
3. E. R. Talaty, A. E. Dupuy, Jr. and C. M. Utermohlen, J. Chem. Soc., Chem. Commun., 1971, 16.
4. M. M. Yusoff and E. R. Talaty, Tetrahedron Lett., 1996, 48, 8695.
5. E. R. Talaty, M. M. Yusoff, S. A. Ismail, J. A. Gomez, C. E. Keller and J. M. Younger, Synlett, 1997, 6, 683.
6. J. C. Sheehan and J. H. Beeson, J. Am. Chem. Soc., 1967, 89, 362.
7. E. R. Talaty, J. A. Gomez, J. A. Dillon, E. Palomino, M. O. Agho, B. C. Batt, K. J. Gleason, S. Park, J. R. Hernandez, M. M. Yusoff, G. A. Rupp, F. C. Malone, M. F. Brummett, C. L. Finch, S. A. Ismail, N. Williams and M. Aghakhani, Synth. Commun., 1987, 1063.
8. H. Quast and H. Leybach, Chem. Ber., 1991, 124, 2105, also studied this reaction.
9. 2 = Me) and have correlated products with nucleophilic constants. However, in no case was the aziridinone actually isolated.
10. H. E. Baumgarten, J. F. Fuerholzer, R. D. Clark and R. D. Thompson, J. Am. Chem. Soc., 1963, 85, 3303;
11. tOH with 1-tert-butyl-3-phenylaziridinone and 1-tert-butyl-3-bisnorcholanylaziridinone, respectively, the results being in accord with the simple guidelines (refs. 1 and 2).
12. Second and third reactions: work done by S.A. Ismail in our laboratory.