Carbazole-1,2-quinodimethane: Generation and reactivity

Synlett

Volumn , Issue 12, 1997, Pages 1444-1446

  Tomé, Augusto C ^a   Enes, Roger F ^a   Cavaleiro, José A S ^a   Martarello, Laurent ^b   Kirsch, Gilbert ^b  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITÉ DE LORRAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003057355     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1058     Document Type: Article

References (17)

1. Reviews on benzo-o-quinodimethanes: a) Charlton, J. L.; Alauddin, M. M. Tetrahedron, 1987, 43, 2873;
2. b) Martin, N.; Seoane, C.; Hanack, M. Organic Prep. and Procedures Int., 1991, 23, 237.
3. Reviews on heteroaromatic o-quinodimethanes: a) Chou, T.-S. Reviews on Heteroatom Chem., 1993, 8, 65;
4. b) Ando, K.; Takayama, H. Heterocycles, 1994, 37, 1417.
5. a) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron, 1996, 52, 1723;
6. b) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Tetrahedron, 1996, 52, 1735;
7. c) Tomé, A. C.; Cavaleiro, J. A. S.; Storr, R. C. Synlett, 1996, 531;
8. d) Vicente, M. G.; Tomé, A. C.; Walter, A.; Cavaleiro, J. A. S. Tetrahedron Lett., 1997, 38, 3639.
9. Martarello, L.; Joseph, D.; Kirsch, G. Heterocycles, 1996, 43, 367.
10. +, 49), 221 (80), 206 (100).
11. Greenhalgh, R. P. Synlett, 1992, 235.
12. These types of dimers were already characterized for different o-quinodimethanes: a) Chou, T.-S.; Chang, R.-C. J. Org. Chem., 1993, 58, 493;
13. b) Chou, T.-S.; Chen, H.-C.; Tsai, C.-Y. J. Org. Chem., 1994, 59, 2241;
14. c) Leung, M.-K.; Trahanovsky, W. J. Am. Chem. Soc., 1995, 117, 841.
15. Typical procedure: Sulfone. 2 (75 mg; 0.26 mmol) and N-phenylmaleimide (68 mg; 1.5 equiv.) were heated in refluxing 1,2,4-trichlorobenzene (5ml), under nitrogen atmosphere, for 3 hours. After cooling to room temperature, the mixture was applied to the top of a column of silica; the trichlorobenzene and the unreacted NPM were eluted with petroleum ether/ dichloromethane (2:1), and the adduct was then eluted with dichloromethane.
16. +, 100), 379 (22), 246 (10), 232 (25), 221 (39), 217 (47), 206 (54).
17. +, 52), 362 (100), 347 (37), 319 (13), 304 (16), 291 (14), 181 (18), 152 (14).