Formal [(2+2)+2] and [(2+2)+(2+2)] nonconjugated dienediyne cascade cycloadditions

Organic Letters

Volumn 7, Issue 20, 2005, Pages 4353-4355

  Wu, Yao Ting ^a   Linden, Anthony ^a   Siegel, Jay S ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26444484255     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514799     Document Type: Article

References (28)

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3. (c) Fickes, G. N.; Metz, T. E. J. Org. Chem. 1978, 43, 4057-61.
4. Blomquist, A. T.; Meinwald, Y. C. J. Am. Chem. Soc. 1959, 81, 667-72.
5. Review of reactions of NBD and alkynes: (a) Lautens, M.; Tam W. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1998; Vol. 6, pp 49-101.
6. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
7. Selected examples: (a) Marchueta, I.; Montenegro, E.; Panov, D.; Poch, M.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 2001, 66, 6400-9.
8. (b) Lee, B. Y.; Moon, H.; Chung, Y. K.; Jeong, N. J. Am. Chem. Soc. 1994, 116, 2163.
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10. Selected examples: (a) Hilt, G.; Smolko, K. I. Synthesis 2002, 686.
11. (b) Hilt, G.; du Mesnil, F.-X. Tetrahedron Lett. 2000, 41, 6757.
12. (c) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-79.
13. (d) Lautens, M.; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8-9.
14. (a) Villeneuve, K.; Jordan, R. W.; Tam, W. Synlett 2003, 2123.
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16. (c) Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 580.
17. From over 37 g of NBD and an excess of acetylene gas, 2.5-2.8 g of D was isolated. See: Schrauzer, G. N.; Glockner, P. Chem. Ber. 1964, 97, 2451.
18. Neat NBD was used as the solvent in the presence of various rhodium complexes to generate different dimers and trimers of NBD. See: Acton, N.; Roth, R. J.; Katz, T. J.; Frank, J. K.; Maier, C. A.; Paul, I. C. J. Am. Chem. Soc. 1972, 94, 5446.
19. This method has been also applied to prepare indenocorannulenes. See: Wu, Y.-T.; Hayama, T.; Baldridge, K. K.; Linden, A.; Siegel, J. S. Submitted to J. Am. Chem. Soc. 2005.
20. It was also observed that NBD as a "proalkyne" participates in the [2+2+2] cycloaddition with two alkynes to generate 1,3-disubstituted benzenes as byproducts; see ref 6c.
21. Only the reaction products from 1 are isolated and characterized. Yields are based on 1 as the limiting reagent. Dimers coming from NBD were also formed but neglected.
22. 2) = 0.1344 (all data). The "polycyclic alkane" part of the molecule is disordered over two conformations (0.7:0.3 occupation ratio), which are inverted images of one another.
23. Similar [4+(2+2)] cycloadducts come from 1,3-butadienes and NBD. See: (a) Lautens, M.; Tam, W.; Sood, C. J. Org. Chem. 1993, 58, 4513-15.
24. (b) Chen, Y.; Snyder, J. K. J. Org. Chem. 1998, 63, 2060.
25. A mixture of 1,2-diphenylethyne, NBD, and Wilkinson catalyst was employed at 130°C as a blank experiment. According to the HPLC and GC analyses, only the starting materials were obtained. Thus, the key intermediate of this reaction, the 1-rhodacyclopentadiene derivative 6, is confirmed. The same reason can also explain how D is formed only in high-pressure conditions.
26. Intramolecular cyclizations of 1a at 100°C to form 7-phenylbenzo[k]fluoranthene. See: Bossenbroek, B.; Sanders, D. C.; Curry, H. M.; Shechter, H. J. Am. Chem. Soc. 1969, 91, 371.
27. Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427.
28. 24: 420.1878; found, 420.1871.