A novel approach to 1-aryl-2-(p-tolylazo)alkenes from alkyl aryl ketones

Tetrahedron

Volumn 54, Issue 20, 1998, Pages 5315-5324

  Caposcialli, Nadia ^a   Dell'Erba, Carlo ^a   Novi, Marino ^a   Petrillo, Giovanni ^a   Tavani, Cinzia ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 ARYL 2 (4 TOLYLAZO)ALKENE; ALKENE DERIVATIVE; ARYLAZOSULFONIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032516260     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00206-3     Document Type: Article

References (21)

1. 1. a) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1992, 48, 325;
2. b) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1993, 49, 235;
3. c) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Phosphorus, Sulfur and Silicon 1993, 74, 409;
4. d) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1994, 50, 11239;
5. e) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1996, 52, 5889.
6. 2. a) Attanasi, O. A.; Caglioti, L. Org. Prep. Proced. Int. 1986, 18, 299.
7. b) Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Sánchez, J. B. Tetrahedron: Asymmetry 1995, 6, 945.
8. 3. a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990, pp 41-42, 122-124, 183, and references cited therein.
9. b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987.
10. 4. In the case of 4k traces of unidentified products were actually observed within 3 hours.
11. 1H-NMR: 2.44 (3H, s), 2.45 (3H, s), 7.33 and 7.81 (2H each, AA′BB′, J 8.2 Hz).
12. 6. Mishima, M.; Yamazaki, H.; Matsuse, T.; Sakuma, T.; Togashi, H. (Kao Corp.) Jpn. Kokai Tokkyo Koho, 1990, 10, 365 (Chemical Abstract 1990, 113, 88237t).
13. 7. Neunhoeffer, H. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W. Eds.; Pergamon Press: Oxford, 1984; Vol. 3, Chapter 2.21 and references therein.
14. 9
15. 9. Boger, D. L. Tetrahedron 1983, 39, 2869.
16. 10. Schantl, J. G. Org. Magn. Reson. 1979, 12, 652. Schantl, J. G.; Margaretha, P. Helv. Chim. Acta 1981, 64, 2492.
17. 10. Schantl, J. G. Org. Magn. Reson. 1979, 12, 652. Schantl, J. G.; Margaretha, P. Helv. Chim. Acta 1981, 64, 2492.
18. 11. Schantl, J. G.; Hebeisen, P. Tetrahedron 1990, 46, 395.
19. 12. Kropp, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102.
20. 1H-NMR: 1.06 (9H, s), 2.81 (2H, s), 3.87 (3H, s), 6.92 and 7.93 (2H each, AA′BB′, J 9.0 Hz).
21. b) Hanack, M.; Weber, E. Chem. Ber. 1983, 116, 777.