Catalytic ring-closing olefin metathesis of sulfur-containing species: Heteroatom and other effects

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1283-1286

  Shon, Young Seok ^a   Lee, T Randall ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIOLE DERIVATIVE; FURAN DERIVATIVE; PYRAN DERIVATIVE; THIOPHENE DERIVATIVE; THIOPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0031584892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00072-5     Document Type: Article

References (19)

1. 1. For reviews, see: Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H. Angew. Chem. Int. Ed. Engl. 1995, 17, 34.
2. 1. For reviews, see: Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446; Schmalz, H. Angew. Chem. Int. Ed. Engl. 1995, 17, 34.
3. 2. Fu, G.C.; Grubbs, R.H. J. Am. Chem. Soc. 1992, 114, 5426.
4. 3. Sibejin, M.; Mol, J.C. Appl. Catal. 1991, 67, 279.
5. 4. Fu, G.C.; Grubbs, R.H. J. Am. Chem. Soc. 1992, 114, 7324.
6. 5. Larroche, C.; Laval, J.P.; Lattes, A; Basset, J.M. J. Org. Chem. 1984,49, 1886.
7. 6. O'Gara, J.E.; Portmess, J.D.; Wagener, K.B. Macromol. 1993, 26, 2837.
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9. 8. Leconte, M.; Isabelle, J.; Pagano, S.; Lefebvre, F.; Basset, J.-M. J. Chem. Soc., Chem. Commun. 1995, 857.
10. 9. For reviews of SAMs, see: Whitesides, G.M.; Laibinis, P.E. Langmuir 1990, 6, 87; Ulman, A. An Introduction to Ultrathin Organic Films; Academic: San Diego, 1991; Ulman, A. Chem. Rev. 1996, 96, 1533.
11. 9. For reviews of SAMs, see: Whitesides, G.M.; Laibinis, P.E. Langmuir 1990, 6, 87; Ulman, A. An Introduction to Ultrathin Organic Films; Academic: San Diego, 1991; Ulman, A. Chem. Rev. 1996, 96, 1533.
12. 9. For reviews of SAMs, see: Whitesides, G.M.; Laibinis, P.E. Langmuir 1990, 6, 87; Ulman, A. An Introduction to Ultrathin Organic Films; Academic: San Diego, 1991; Ulman, A. Chem. Rev. 1996, 96, 1533.
13. 10. Fox, H.H.; Yap, K.B.; Robbins, J.; Cai, S.; Schrock, R.R. Inorg. Chem. 1992, 31, 2287; Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
14. 10. Fox, H.H.; Yap, K.B.; Robbins, J.; Cai, S.; Schrock, R.R. Inorg. Chem. 1992, 31, 2287; Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
15. 11. Fu, G.C.; Nguyen, S.T.; Grubbs, R.H. J. Am. Chem. Soc. 1993, 115, 9856.
16. 12. A more active version of 2, where the alkylidene is a benzylidene, has recently been reported: Schwab P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039; Schwab, P.; Ziller, J.W.; Grubbs, R.H. J. Am. Chem. Soc. 1996, 118, 100. Preliminary experiments in our laboratories suggest that this Ru-based catalyst also fails to catalyze the RCM of the acyclic disulfides reported in Table 1.
17. 12. A more active version of 2, where the alkylidene is a benzylidene, has recently been reported: Schwab P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039; Schwab, P.; Ziller, J.W.; Grubbs, R.H. J. Am. Chem. Soc. 1996, 118, 100. Preliminary experiments in our laboratories suggest that this Ru-based catalyst also fails to catalyze the RCM of the acyclic disulfides reported in Table 1.
18. 13. Burns, J.A.; Whitesides, G.M. J. Am. Chem. Soc. 1990, 112 6296, and references therein.
19. 4, filtered, and evaporated. Chromatography of the concentrated solution on silica gel (1:49, ethyl acetate:hexane) afforded 0.0897 g (91% yield) of the ring-closed compound as a colorless oil.