Generation and Cyclization of a Benzyne-Tethered Alkyllithium: Preparation of 4-Substituted Indans

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 432-433

  Bailey, William F ^a   Longstaff, Sarah C ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000106293     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972065z     Document Type: Article

References (29)

1. (a) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
2. (b) Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon: New York, 1974.
3. (a) Bunnett, J. F.; Hrutfiord, B. F. J. Am. Chem. Soc. 1961, 83, 1691.
4. (b) Bunnett, J. F.; Kato, T.; Flynn, R. R.; Skorcz, J. A. J. Org. Chem. 1963, 28, 1.
5. (a) Huisgen, R.; König, H.; Lepley, A. R. Chem. Ber. 1960, 93, 1496.
6. (b) Huisgen, R.; Sauer, J. Angew. Chem. 1960, 72, 91.
7. (a) Kessar, S. V. Acc. Chem. Res. 1978, 11, 283, and references therein.
8. (b) Clark, R. D.; Caroon, J. M. J. Org. Chem. 1982, 47, 2804.
9. (c) Pansegrau, P. D.; Rieker, W. F.; Meyers, A. I. J. Am. Chem. Soc. 1988, 110, 7178.
10. (d) Biehl, E. D.; Khanapure, S. P. Acc. Chem. Res. 1989, 22, 275.
11. (e) Iwao, M. J. Org. Chem, 1990, 55, 3622.
12. (f) Sielecki, T. M.; Meyers, A. I. J. Org. Chem. 1992, 57, 3673.
13. (g) Stanetty, P.; Krumpak, B. J. Org. Chem. 1996, 61, 5130.
14. (a) Bailey, W. F.; Ovaska, T. V.; Leipert, T. K. Tetrahedron Lett. 1989, 30, 3901.
15. (b) Bailey, W. F.; Ovaska, T. V. Tetrahedron Lett. 1990, 32, 627.
16. (c) Wu, G.; Cederbaum, F. E.; Negishi, E. Tetrahedron Lett. 1990, 31, 493.
17. (d) Bailey, W. F.; Ovaska, T. V. Chem. Lett. 1993, 819.
18. (e) Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080.
19. (f) Bailey, W. F.; Wachter-Jurcsak, N. M.; Pineau, M. R.; Ovaska, T. V.; Warren, R. R.; Lewis, C. E. J. Org. Chem. 1996, 61, 8216.
20. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
21. (a) Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 1.
22. (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
23. (c) Wittig, G.; Pieper, G.; Fuhrmann, G. Chem. Ber. 1940, 73, 1193.
24. (d) Gilman, H.; Soddy, T. S. J. Org. Chem. 1957, 22, 1715.
25. 6
26. Bauer, W.; Winchester, W. R.; Schleyer, P. v. R.; Organometallics 1987, 6, 2371.
27. Bates, T. F.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109.
28. All of the indans prepared in this study (Table 1) are known compounds whose physical and spectroscopic properties are fully in accord with those reported in the literature. Details may be found in the Supporting Information that accompanies this article.
29. Wightman, R. H.; Laycock, D. E.; Avdovich, H. W. J. Org. Chem. 1978, 43, 2167 and references therein.