PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes

Organometallics

Volumn 15, Issue 3, 1996, Pages 901-903

  Chatani, Naoto ^a   Furukawa, Naoyuki ^a   Sakurai, Hitoshi ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001525502     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950832j     Document Type: Article

References (24)

1. Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc. 1994, 116, 6049.
2. (a) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636.
3. (b) Trost, B. M.; Trost, M. K. Tetrahedron Lett. 1991, 32, 3647.
4. (c) Trost, B. M.; Trost, M. K. J. Am. Chem. Soc. 1991, 113, 1850.
5. Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737.
6. Watanuki, S.; Ochifuji, N.; Mori, M. Organometallics 1994, 13, 4129.
7. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974.
8. Kinoshita, A.; Mori, M. Synlett 1994, 1020.
9. For a recent paper on Pd(IV), see: Canty, A. J.; Jin, H.; Roberts, A. S.; Skelton, B. W.; Traill, P. R.; White, A. H. Organometallics 1995, 14, 199 and references cited therein.
10. 1-alkyne complex bearing a positive charge at the β position may exist in equilibrium with the carbene which can undergo intramolecular cyclopropanation to give a cyclopropylalkylidene complex, which seems to be a reactive intermediate in the present reaction. A study of the reaction mechanism is underway. See also Trost, B. M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1085.
11. Pilette, D.; Moreau, S.; Le Bozec, H.; Dixneuf, P. H.; Corrigan, J. F.; Carty, A. J. J. Chem. Soc., Chem. Commun. 1994, 409.
12. Enda, J.; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1984, 1589.
13. Silvestre, J.; Hoffmann, R. Helv. Chim. Acta 1985, 68, 1461.
14. Ryabov, A. D.; van Eldik, R.; Le Borgne, G.; Pfeffer, M. Organometallics 1993, 12, 1386.
15. 1 coordination of the alkyne. de Vaal, P.; Dedieu, A. J. Organomet. Chem. 1994, 478, 121.
16. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
17. 1H NMR. In all cases, the only peaks we can see were those from 1 and/or 2, and no other peaks can be detected.
18. Small amounts of insoluble polymeric materials have been formed in some cases, causing incomplete material balances.
19. 2 may be due to its poor solubility.
20. All new compounds were characterized by NMR, IR, and mass spectral data and by elemental analyses or high-resolution mass spectra. See the Supporting Information.
21. 2 to dimethyl acetylenedicarboxylate is a precedent. Canziani, F.; Garlaschelli, L.; Malatesta, M. C. J. Organomet. Chem. 1978, 146, 179. Holland, P. R.; Howard, B.; Mawby, R. J. J. Chem. Soc., Dalton Trans. 1983, 231. equation presented
22. 2 to dimethyl acetylenedicarboxylate is a precedent. Canziani, F.; Garlaschelli, L.; Malatesta, M. C. J. Organomet. Chem. 1978, 146, 179. Holland, P. R.; Howard, B.; Mawby, R. J. J. Chem. Soc., Dalton Trans. 1983, 231. equation presented
23. 2H-labeling study. See ref 2a. However, Trost has not observed a type b product except for the labeling reaction.
24. 4: Blum, J.; Beer-Kraft, H.; Badrieh, Y. J. Org. Chem. 1995, 60, 5567.