Improved procedure for cyclization of vinyl azides into 3-substituted-2H-azirines

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5339-5341

  Timén, Åsa Sjöholm ^a   Risberg, Erik ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Azirine; Thermolysis; Vinyl azide

Indexed keywords

AZIRINE DERIVATIVE; SOLVENT; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION; HEATING; HIGH TEMPERATURE; METHODOLOGY; REACTION TIME; SYNTHESIS;

EID: 0038007830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01205-X     Document Type: Article

References (23)

1. Gilchrist T.L. Aldrichim. Acta. 34:2001;51-55.
2. Rai K.L.M., Hassner A. Advances in Strained and Interesting Organic Molecules. 8:2000;187-257.
3. Ray C.A., Risberg E., Somfai P. Tetrahedron. 58:2002;5983-5987.
4. Sjöholm Timén Å., Fischer A., Somfai P. Chem. Commun. 2003;1150-1151.
5. Palacios F., Ochoa de Retana A.M., Martínez de Marigorta E., de los Santos J.M. Org. Prep. Proced. Int. 34:2002;219-269.
6. Smolinsky G. J. Org. Chem. 27:1962;3557-3559.
7. Hassner A., Fowler F.W. J. Org. Chem. 33:1968;2686-2691
8. Hassner, A. Vinyl Azides and Nitrenes. In Azides and Nitrenes; Scriven, E. F. V., Ed.; Academic Press: Orlando, Florida, 1984; pp. 35-94.
9. Smolinsky G. J. Am. Chem. Soc. 83:1961;4483-4484.
10. Hortmann A.G., Robertson D.A., Gillard B.K. J. Org. Chem. 37:1972;322-324.
11. Pinho e Melo T.M.V.D., Lopes C.S.J., Cardoso A.L., Rocha Gonsalves A.M.d'A. Tetrahedron. 57:2001;6203-6208.
12. Banert K. Chem. Ber. 120:1987;1891-1896.
13. Hassner A., Fowler F.W. J. Am. Chem. Soc. 90:1968;2869-2875.
14. Gilchrist T.L., Mendonça R. Synlett. 2000;1843-1845.
15. Kumar R., Nath M., Tyrrell D.L.J. J. Med. Chem. 45:2002;2032-2040.
16. Banert K. Chem. Ber. 122:1989;1175-1178.
17. Alves M.J., Gilchrist T.L. Tetrahedron Lett. 39:1998;7579-7582.
18. Hassner A., Fowler F.W. Tetrahedron Lett. 1967;1545-1548.
19. Ray C.A., Risberg E., Somfai P. Tetrahedron Lett. 42:2001;9289-9291.
20. Risberg E., Somfai P. Tetrahedron: Asymmetry. 13:2002;1957-1959.
21. 2O under the same conditions.
22. 1H NMR spectroscopy.
23. 2, pentane and THF have also been used, with results in line with those presented in Table 2.