Skeletal reorganization of enynes into 1-vinylcycloalkenes in ionic liquids

Journal of Organic Chemistry

Volumn 69, Issue 24, 2004, Pages 8541-8543

  Miyanohana, Yuhei ^a   Inoue, Hiroki ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; DISTILLATION; EXTRACTION; IONS; PLATINUM COMPOUNDS; REACTION KINETICS; SOLVENTS; TRANSITION METAL COMPOUNDS;

IONIC LIQUIDS; SKELETAL REORGANIZATION;

OLEFINS;

CYCLOALKENE; PLATINUM DERIVATIVE; SOLVENT; TRANSITION ELEMENT; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DISTILLATION; EXTRACTION; LIQUID; LOW TEMPERATURE; REACTION TIME;

EID: 9344240475     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0489061     Document Type: Article

References (24)

1. The conversion of enynes into 1-vinylcycloalkenes can be classified into two types, enyne-metathesis and skeletal reorganization, although two reactions are not strictly distinguished. The two reactions differ based on their mechanism and product distributions. Skeletal reorganization gives two possible isomers I and II, although the selectivity depends on the structure of the enynes and the nature of the catalysts. In many cases, either of the two products are obtained. The enyne-metathesis is typically catalyzed by Grubbs-type catalysts
2. Recent reviews, see: Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
3. Recent reviews, see: Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
4. Pioneering study: Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636.
5. Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
6. Trost, B. M.; Chang, V. K. Synthesis 1993, 824.
7. Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901.
8. Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104.
9. Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
10. Fürstner, A.; Szillat, H.; Stelzer, F. J. Am. Chem. Soc. 2000, 122, 6785. Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
11. Oh, C. H.; Bang, S. Y.; Rhim, C. Y. Bull. Korean Chem. Soc. 2003, 24, 887.
12. Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704.
13. Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
14. Nieto-Oberhuber, C.; Munoz, M. P.; Bunuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
15. Schmitz, W. D.; Messerschmidt, B.; Romo, D. J. Org. Chem. 1998, 63, 2058.
16. Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294.
17. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
18. Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305. Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801.
19. For reviews on ionic liquids and their application in transition metal-catalyzed reactions, see: Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. Sheldon, R. Chem. Commun. 2001, 2399. Dupont, J.; de Souza, R. F.; Suarez, P. A. Chem. Rev. 2002, 102, 3667.
20. For reviews on ionic liquids and their application in transition metal-catalyzed reactions, see: Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. Sheldon, R. Chem. Commun. 2001, 2399. Dupont, J.; de Souza, R. F.; Suarez, P. A. Chem. Rev. 2002, 102, 3667.
21. For reviews on ionic liquids and their application in transition metal-catalyzed reactions, see: Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. Sheldon, R. Chem. Commun. 2001, 2399. Dupont, J.; de Souza, R. F.; Suarez, P. A. Chem. Rev. 2002, 102, 3667.
22. Gold mirror was observed on the wall of the reaction vessel after the reaction.
23. Méndez, M.; Munoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. Munoz, M. P.; Méndez, M.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Synthesis 2003, 2898.
24. Méndez, M.; Munoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. Munoz, M. P.; Méndez, M.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Synthesis 2003, 2898.