Solvent-free aziridination of α-nitroalkenes

Tetrahedron

Volumn 54, Issue 22, 1998, Pages 6169-6176

  Fioravanti, Stefania ^a   Pellacani, Lucio ^a   Stabile, Sara ^a   Tardella, Paolo A ^a   Ballini, Roberto ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b Dipartimento di Scienze Chimiche dell'Universita   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032575231     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00309-3     Document Type: Article

References (17)

1. 1. For recent reviews of nitro compounds see: a) Boyd, G.V. in The Chemistry of Amino, Nitroso, Nitro and Related Groups Part I, Patai, S., Ed.; John Wiley & Sons: New York 1996, pp 533-626;
2. b) Perlmutter, P. in Conjugated Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series, Vol 9; Pergamon Press; Oxford 1992, chapter 6.
3. 2. Fioravanti, S.; Pellacani, L.; Stabile, S.; Tardella, P. A.; Ballini, R. Tetrahedron Lett. 1997, 38, 3309-3310.
4. 3. Lwowski, W.; Maricich, T. J. J. Am. Chem. Soc. 1965, 87, 3630-3637.
5. 4. a) Enders, D.; Wiedemann, J. Synthesis 1996, 1443-1450;
6. b) Atkinson, R. S.; Williams, P. J. J. Chem. Soc., Perkin Trans. I 1996, 1951-1959.
7. 5. In the past we advanced this hypothesis, but no experimental evidence has been gained until now: Pellacani, L.; Pulcini, P.; Tardella, P. A. J. Org. Chem. 1982, 47, 5023-5025.
8. 6. Apeloig, Y.; Karni, M.; Rappoport, Z. J Am. Chem. Soc. 1983, 105, 2784-2793; we wish to thank Professor Rappoport for helpful discussion on this point.
9. 7. Lwowski, W.; Mattingly, T. W., Jr. J. Am. Chem. Soc. 1965, 87, 1947-1958.
10. 8. a) Cerichelli, G.; Freddi, A.; Loreto, M. A.; Pellacani, L.; Tardella, P. A. Tetrahedron 1992, 48, 2495-2500;
11. b) Also in the case of polyunsaturated ketones we obtained scarcely regioselective aziridination: data to be published from this laboratory.
12. 9. a) Clark, J. H.; Macquarrie, D. Chem. Soc. Rev. 1996, 25, 303-310;
13. b) Toda, F. Acc. Chem. Res., 1995, 28, 480-486,
14. c) Dittmer, D. C. Chem. Ind. (London) 1997, 779-784.
15. 10. a) Ballini, R.; Castagnani, R.; Petrini, M. J. Org. Chem. 1992, 57, 2160-2162;
16. b) Ballini, R.; Palestini C. Tetrahedron Lett. 1994, 35, 5731-5734.
17. 2 IR and MS spectra of compounds 3 are not reported because similar to those of the corresponding isomers 2.