Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates

Tetrahedron

Volumn 59, Issue 13, 2003, Pages 2345-2351

  Pinho e Melo, Teresa M V D ^a   Cardoso, Ana L ^a   Rocha Gonsalves, António M D'A ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

2 halo 2H azirine 2 carboxylates; Chiral 2H azirine 2 carboxylates; Dehalogenation

Indexed keywords

10 PHENYLSULFONYLISOBORNYL 2 BROMO 3 PHENYL 2H AZIRINE 2 CARBOXYLATE; 10 PHENYLSULFONYLISOBORNYL ACETATE; 2H AZIRINE 2 CARBOXYLATE; ACETIC ACID DERIVATIVE; AZIRINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; SODIUM BOROHYDRIDE; TRIBUTYLTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEHALOGENATION; PRIORITY JOURNAL; STEREOISOMERISM; SYNTHESIS;

EID: 0037463773     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00248-5     Document Type: Article

References (17)

1. Pinho e Melo T.M.V.D., Lopes C.S.J., Rocha Gonsalves A.M.A., Storr R.C. Synthesis. 2002;605-608.
2. (a) Padwa A., Woolhouse A.D. Comprehensive Heterocyclic Chemistry. Vol. 7:1984;Pergamon, New York
3. (b) Palacios F., Retana A.M.O., Marigueta E.M., Santos J.M. Eur. J. Org. Chem. 2001;2401-2414.
4. (a) Legters J., Thijs L., Zwanenburg B. Recl. Trav. Chim. Pays-Bas. 111:1992;75-78
5. (b) Gentilucci L., Grijzen Y., Thijs L., Zwanenburg B. Tetrahedron Lett. 36:1995;4665-4668
6. (c) Verstappen M.M.H., Ariaans G.J.A., Zwanenburg B. J. Am. Chem. Soc. 118:1996;8491-8492
7. (d) Davis F.A., Liu H., Liang C.-H., Venkat Reddy G., Zhang Y., Fang T., Titus D.D. J. Org. Chem. 64:1999;8929-8935
8. (e) Davis F.A., Venkat Reddy G., Liu H. J. Am. Chem. Soc. 117:1995;3651-3652.
9. Pinho e Melo T.M.V.D., Lopes C.S.J., Cardoso A.L., Rocha Gonsalves A.M.A. Tetrahedron. 57:2001;6203-6208.
10. Ciabattoni J., Cabell M. Jr. J. Am. Chem. Soc. 93:1971;1482-1483.
11. Miura K., Ichinose Y., Nozaki K., Fugami K. Bull. Chem. Soc. Jpn. 62:1989;143-147.
12. (a) Solas D., Wolinsky J. J. Org. Chem. 48:1983;1988-1991
13. (b) Oppolzer W., Kelly M.J., Bernardinelli G. Tetrahedron Lett. 25:1984;5889-5892.
14. Pinho e Melo T.M.V.D., Lopes C.S.J., Rocha Gonsalves A.M.A., Beja A.M., Paixão J.A., Silva M.R., Alte da Veiga L. J. Org. Chem. 67:2002;66-71.
15. Nishiwaki T. Tetrahedron Lett. 1969;2049-2052.
16. 1H NMR chemical shifts are in agreement with the values described for methyl 2-phenyl-2H-azirine-3-carboxylate Knittel D. Synthesis. 1985;186-188.
17. Ethyl (3R,2R)- and (3S,2R)-3-phenylaziridine-2-carboxylate were prepared as described in Gelas-Mialhe Y., Touraud E., Vessiere R. Can. J. Chem. 60:1982;2830-2851. by comparison of the characterization data of these compounds and the one of 7a we confirmed that we had obtained a mixture of aziridines.