The synthesis of naphthosultine and benzodisultines and their pyrolysis with dienophiles: Studies on o-naphthoquinodimethane and bis-o-quinodimethane

Journal of the Chinese Chemical Society

Volumn 49, Issue 1, 2002, Pages 77-82

  Wu, An Tai ^a   Liu, Wen Dar ^a   Chung, Wen Sheng ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

Benzodisultine; Diels Alder reaction; Naphthosultine; o Quinodimethanes; Pyrolysis; Tetramethylenebenzene

Indexed keywords

EID: 0346522068     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200200013     Document Type: Article

References (20)

1. (a) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873.
2. (b) Oppolzer, W. Synthesis 1978, 793.
3. (c) Martin, N.; Seoane, C.; Hanak, M. Org. Prep. Proced. Int. 1991, 23, 237.
4. (d) Segura, J. L.; Martin, N. Chem. Rev. 1999, 99, 3199.
5. Kametani, T. Pure Appl. Chem. 1979, 51, 747.
6. For 1,4-elimination methods, see (a) Ho, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1982, 104, 7609.
7. (b) Inaba, S.-i.; Wehmeyer, R. M.; Forkner, M. W.; Rieke, R. D. J. Org. Chem. 1988, 53, 339.
8. Flynn, C. R.; Michl, J. J. Am. Chem. Soc. 1974, 96, 3280.
9. Oppolzer, W. Heterocycles 1980, 14, 1615.
10. (a) Cava, M. P.; Shirley, R. L. J. Am. Chem. Soc. 1960, 82, 654.
11. (b) Gisin, M.; Wirz, J. Helv. Chim. Acta 1976, 59, 2273.
12. (a) Chung, W.-S.; Lin, W.-J.; Liu, W.-D.; Chen, L.-G. J. Chem. Soc. Chem. Commun. 1995, 2537.
13. (b) Chung, W.-S.; Liu, J.-H. Chem. Commun. 1997, 205.
14. (c) Liu, J.-H.; Wu, A.-T.; Huang, M.-H.; Wu, C.-W.; Chung, W.-S. J. Org. Chem. 2000, 65, 3395.
15. For a review of sultines see: Dittmer, D. C.; Hoey, M. D. The Chemistry of Sulphinic Acids, Esters and Their Derivatives; Wiley: Chichester, 1990; pp 239-273.
16. For related tandem Diels-Alder reactions see (a) Rubello, A.; Vogel, P. Helv. Chim. Acta 1988, 71, 1268.
17. (b) Reynolds, J. H.; Berson, J. A.; Kumashiro, K. K.; Duchamp, J. C.; Zilm, K. W.; Scaiano, J. C.; Berinstain, A. B.; Rubello, A. A.; Vogel, P. J. Am. Chem. Soc. 1993, 115, 8073.
18. (c) Lu, H. S. M.; Berson, J. A. J. Am. Chem. Soc. 1996, 118, 265.
19. For an interesting application of this bis-o-QDM strategy, see: Gügel, A.; Belik, P.; Walter, M.; Kraus, A.; Harth, E.; Wagner, M.; Spickermann, J.; Müllen, K. Tetrahedron 1996, 52, 5007.
20. Hebbelynck, M. F.; Martin, R. H. Bull. Soc. Chim. Belges. 1950, 59, 206.