Electronically mediated selectivity in ring opening of 1-azirines. The 3-Z mode: Convenient route to 2-aza-1,3-dienes

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 49-53

  Barroso, Marcia T ^a   Kascheres, Albert ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1 AZIRINE; 2 AZA 1,3 DIENE; 2 ETHYLIMIDAZOLE; 3,5 DIMETHYLPYRAZOLE; ACRYLIC ACID; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033534455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980198u     Document Type: Article

References (12)

1. Kascheres, A.; Sá, M. C. M. J. Org. Chem. 1996, 61, 3749.
2. Kascheres, A.; Nunes da Silva, J., Jr.; Brandão, F. Tetrahedron 1997, 53, 7089.
3. 1H NMR spectra of 2. In the case of 2a, the proportion for both Z and E isomers is approximately 10:1.
4. (a) Ghosez, L.; Bayard, Ph.; Nshimyumukiza, P.; Gouverneur, V.; Sainte, F.; Beaudegnies, R.; Rivera, M.; Frisque-Hesbain, A. M.; Wynants, C. Tetrahedron 1995, 51, 11021.
5. (b) Barluenga, J.; Joglar, J.; González, F. J.; Fustero, S. Synlett 1990, 129.
6. (c) Palacios, F.; de Heredia, I. P.; Rubiales, G. J. Org. Chem. 1995, 60, 2384.
7. (d) Boger, D. L. Comprehensive Organic Synthesis; Trost, B. M., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 451.
8. 1H NMR spectrum of 4 is the presence of diastereotopic methylene hydrogens, thus demonstrating the nonplanar nature of this potentially 8π electron system.
9. The geometry of the exo double bond in 5 was established through a NOE-difference experiment [irradiation of the imino methyl produced an enrichment of the olefinic hydrogen (8.3%)].
10. Padwa, A.; Smolanoff, J.; Tremper, A. J. Am. Chem. Soc. 1975, 6, 4682.
11. Kascheres, A.; Oliveira, C. M. A.; de Azevedo, M. B. M.; Nobre, C. M. S. J. Org. Chem. 1991, 56, 7.
12. Partial data. Some signals here are hidden within the signals of the major isomer.