A transition-metal-η4-diene cation can undergo nucleophilic addition at the internal carbon

Organometallics

Volumn 17, Issue 6, 1998, Pages 1002-1003

  Fan, Jang Shyang ^a   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005368989     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om971033z     Document Type: Article

References (12)

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2. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Mill Valley, CA, 1994; Chapter 7, p 199.
3. Semmelhack, M. F.; Le, H. T. M. J. Am. Chem. Soc. 1984, 106, 1785.
4. Semmelhack, M. F.; Herndon, J. W. Organometallics 1983, 2, 363.
5. Semmelhack, M. F.; Herndon, J. W.; Springer, J. P. J. Am. Chem. Soc. 1983, 105, 2497.
6. Davies, S. G.; Green, M. L. H.; Mingos, D. M. P. Tetrahedron 1978, 34, 3047.
7. (a) Faller, J. W.; Murray, H. H.; White, D. L.; Chao, K. H. Organometallics 1983, 2, 400.
8. (b) Pearson, A. J.; Khan, M. N. I. J. Am. Chem. Soc. 1984, 106, 1872.
9. Pearson, A. J.; Khan, M. N. I.; Clardy, J. C.; He, C.-H. J. Am. Chem. Soc. 1985, 107, 2748.
10. Wang, S.-H.; Cheng, Y.-C.; Lee, G.-H.; Peng, S.-M.; Liu, R.-S. Organometallics 1993, 12, 3282.
11. 3-allyl compound in high yield; it is unclear whether reaction at -78°C would yield (1,3,4-η)-σ,π-cyclohexenyl species.
12. The mechanism for alkylation at internal carbons of 1 presumably follows the rule that PhMgBr preassociates with the tungstendiene cation 1 before addition of the second PhMgBr. In the future, we will carry out a detailed kinetic study to elucidate the mechanism.