Tandem rearrangement, cyclization and aromatization of sulfur bridged propargylic systems

Tetrahedron Letters

Volumn 41, Issue 15, 2000, Pages 2675-2678

  Braverman, Samuel ^a   Zafrani, Yossi ^a   Gottlieb, Hugo E ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

Cyclization; Diallenes; Diradicals; Diynes; Sulfur compounds

Indexed keywords

SULFUR DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ISOMERISM; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0034620924     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00221-5     Document Type: Article

References (25)

1. (a) Braverman, S.; Stabinsky, Y. Isr. J. Chem. 1967, 5, 125.
2. (b) Braverman, S.; Mechoulam, H., ibid, 1967, 5, 71; Tetrahedron 1974, 30, 3883.
3. (b) Braverman, S.; Mechoulam, H., ibid, 1967, 5, 71; Tetrahedron 1974, 30, 3883.
4. (a) Braverman, S. In Chemistry of Sulfones and Sulfoxides; Patai, S.; Rappoport, Z.; Stirling, C. J. M., Eds.; Wiley: New York, 1988; Chapter 13.
5. (b) Braverman, S. ibid., Chapter 14.
6. Braverman, S.; Segev, D. J. Am. Chem. Soc. 1974, 96, 1245.
7. (a) Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1990, 112, 5830.
8. (b) Braverman, S.; Duar, Y. Tetrahedron Lett. 1978, 1493.
9. (c) Braverman, S.; Duar, Y.; Segev, D. Tetrahedron Lett. 1976, 3181.
10. (d) For related studies on bis-allenic sulfides, see: Garratt, P. J.; Neoh, S. B. J. Org. Chem. 1979, 44, 2667; Cheng, Y. S. P.; Garratt, P. J.; Neoh, S. B.; Rumjamebe, V. M. Isr. J. Chem. 1985, 26, 101.
11. (d) For related studies on bis-allenic sulfides, see: Garratt, P. J.; Neoh, S. B. J. Org. Chem. 1979, 44, 2667; Cheng, Y. S. P.; Garratt, P. J.; Neoh, S. B.; Rumjamebe, V. M. Isr. J. Chem. 1985, 26, 101.
12. Nicolaou, K. C.; Skokolas, F.; Malogres, P.; Zucuarello, G.; Schweger, E. J.; Toshima, K.; Wenderborn, S. Angew. Chem., Int. Ed. Engl. 1989, 28, 1272.
13. (a) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J.; Diedrich, F., Eds.; VCH: Weinheim, 1995; Chapter 7.
14. (b) Wang, K. K. Chem. Rev. 1996, 96, 207.
15. Nicolaou, K. C.; Wenderborn, S.; Maligres, P.; Isshiki, K.; Zein, N.; Ellestad, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 418.
16. (a) Kerwin, S. M. Tetrahedron Lett. 1994, 35, 1023.
17. (b) McPhee, M. M.; Kerwin, S. M. Org. Chem. 1996, 61, 9385.
18. (c) Sakai, Y.; Bando, Y.; Shishido, K.; Shibuya, M. Tetrahedron Lett. 1992, 33, 957.
19. Maxam, A. M.; Gilbert, W. Methods Enzymol. 1980, 65, 499.
20. 15OS) 279.084, obsd, 279.084.
21. 3): δ 102.8, 102.2, 46.2.
22. Iwai, I. J. Chem. Pharm. Bull. Jpn. 1984, 12, 1094.
23. For a description of this technique, see for example: Goldschmidt, Z.; Genizi, E.; Gottlieb, H. E. J. Organomet. Chem. 1999, 81, 587.
24. Kellog, R. M. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Bird, C. W.; Cheesman, G. W. H., Eds.; Pergamon: Oxford, 1984; Vol. 4, pp. 713-740.
25. Braverman, S.; Zafrani, Y.; Gottlieb, H. E., manuscript in preparation.