Unexpected thermal benzannulation of 1,3,5-metallahexatrienes: Synthesis of o-alkoxyphenol-containing polycycles

Organic Letters

Volumn 1, Issue 4, 1999, Pages 541-543

  Barluenga, José ^a   Aznar, Fernando ^a   Angel Palomero, M ^a   Barluenga, Sofía ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001514380     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906256     Document Type: Article

References (20)

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2. (b) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, p 469.
3. (c) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, p 549.
4. (d) Doyle M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, p 387.
5. (e) Harvey, D. F.; Sigano. D. M. Chem. Rev. 1996, 96, 271.
6. (f) Zaragoza Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: 1999.
7. Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644.
8. Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163.
9. Barluenga, J.; Aznar, F.; Barluenga, S.; Fernández, M.; Martín, A.; García-Granda, S.; Piñera-Nicolás, A. Chem. Eur. J. 1998, 4, 2280.
10. (a) Wulff, W. D.; Faron, K. L.; Su, J.; Springer, J. P.; Rheingold, A. L. J. Chem. Soc., Perkin Trans. 1 1999, 197.
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13. 7: C, 54.54; H, 4.07. Found: C, 59.48; H, 4.18.
14. 3-dienylcarbene to yield phenols has been observed: Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Llorca-Baragaño, M. A., submitted for publication.
15. 5 in metallatrienes 3 and 6 is about 0.7 A° (molecular mechanics calculations were carried out using the MM2 force field; data for the pentacarbonyl chromium carbene moiety were taken from an X-ray structure of a similar compound and kept fixed along the minimization).
16. (a) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 7418.
17. (b) Merlic, C. A.; Roberts, W. M. Tetrahedron Lett. 1993, 34, 7379.
18. (c) Merlic, C. A.; Xu, D.; Gladstone, B. G. J. Org. Chem. 1993, 58, 538.
19. 3: C, 72.38; H, 6.95. Found: C, 72.32; H, 6.94.
20. When the reaction was performed without removal of the excess of olefin, a complex mixture of products was obtained.