The Intramolecular Diyl Trapping Reaction. A Useful Tool for Organic Synthesis

Chemical Reviews

Volumn 86, Issue 5, 1986, Pages 875-884

  Little, R Daniel ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001323847     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr00075a010     Document Type: Article

References (29)

1. The situation has changed dramatically. See: Paquette, L. A. Recent Developments in Polyquinane Chemistry; Springer-Verlag: Berlin, Heidelberg, GDR, 1984.
2. Berson, J. A.; McDaniel, D. M.; Corwin, L. R.; Davis, J. H. J. Am. Chem. Soc. 1972, 94, 5508. Berson, J. A.; McDaniel, D. M.; Corwin, L. R. J. Am. Chem. Soc. 1972, 94, 5509. For reviews, see: Berson, J. A. Acc. Chem. Res. 1978, 11, 446. Berson, J. A. In Diradicals; Borden, W. T., Ed.; Wiley: New York, 1982; Chapter 4.
3. Little, R. D.; Bukhari, A.; Venegas, M. G. Tetrahedron Lett. 1979, 20, 305.
4. Little, R. D.; Muller, G. W. J. Am. Chem. Soc. 1979, 101, 7129. (b) Little, R. D.; Muller, G. W. J. Am. Chem. Soc. 1981, 103, 2744. (c) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carroll, G. L.; Bukhari, A.; Patton, L.; Stone, K. J. Tetrahedron 1981, 37, 4371.
5. Ginsburg, D. Tetrahedron 1983, 39 (Report No. 149), 2095–2135, and the references cited therein.
6. Little, R. D.; Higby, R. G.; Moeller, K. D. J. Org. Chem. 1983, 46, 3139.
7. Moeller, K. D. Ph.D. Dissertation, University of California—Santa Barbara, 1985, unpublished results. When we write that electronic factors are unimportant in determining the course of the intramolecular diyl trapping reaction, we are not referring to different reactivity patterns which may occur as a result of the existence of both singlet and triplet forms of the diyl.
8. See, for example: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley-Interscience: New York, 1976; Chapter 4.
9. Little, R. D.; Carroll, G. L. Tetrahedron Lett. 1981, 22, 4392. (b) Little, R. D.; Carroll, G. L.; Petersen, J. L. J. Am. Chem. Soc. 1983, 105, 923.
10. Johnson, F. Chem. Rev. 1968, 68, 375.
11. Berson, J. A.; Bushby, R. J.; McBride, J. M.; Tremmeling, M. J. Am. Chem. Soc. 1971, 93, 1544. (b) Corwin, L. R.; McDaniel, D. M.; Bushby, J. J.; Berson, J. A. J. Am. Chem. Soc. 1980, 102, 276. (c) Platz, M. S. Ph.D. Dissertation, Yale University, 1977. (d) Closs, G. L. J. Am. Chem. Soc. 1971, 93, 1546.
12. Moeller, K. D. Ph.D. Dissertation, University of California—Santa Barbara, 1985, unpublished results. See also: Little, R. D.; Losinski-Dang, L.; Venegas, M. G.; Merlic, C. Tetrahedron Lett. 1983, 24, 4499.
13. Beckwith, A. L. J.; Blair, I. A.; Phillipou, G. Tetrahedron Lett. 1974, 2251. Julia, M.; Descoins, C.; Baillarge, M.; Jacquet, B.; Uguen, D.; Groeger, F. A. Tetrahedron, 1975, 31, 1737. See also ref 28.
14. Unpublished results of the following: Dannecker-Doerig, I. M. S. Thesis, UCSB, 1985. Moeller, K. D. Ph.D. Dissertation, UCSB, 1985. Campopiano, Onorato, research in progress.
15. For example, see: Asymmetric Organic Reactions; Morrison, J. D.; Mosher, H. S., Eds.; American Chemical Society: Washington, DC, 1976. See also: Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908. Corey, E. J.; Ensley, H. E.; Parnell, C. A. J. Org. Chem. 1978, 43, 1610. Rousch, W. R.; Gillis, H. R.; Ko, A. I. J. Am. Chem. Soc. 1982, 104, 2269. Oppolzer, W.; Kurth, M.; Reichlin, D.; Moffatt, F. Tetrahedron Lett. 1981, 22, 2545.
16. Little, R. D.; Moeller, K. D. J. Org. Chem. 1983, 48, 4487.
17. Little, R. D.; Stone, K. J. J. Am. Chem. Soc. 1983, 105, 6976. (b) Stone, K. J.; Little, R. D. J. Am. Chem. Soc. 1985, 107, 2495.
18. Thaisrivongs, S.; Seebach, D. J. Am. Chem. Soc. 1983, 105, 7407.
19. Bunnett, J. F. In Techniques in Organic Chemistry; Weissberger, A., Ed.; Interscience: New York, 1961; Vol. 8, pp 204–210. See also: Giese, B. Acc. Chem. Res. 1984, 17, 438.
20. Van Hijfte, L.; Little, R. D. J. Org. Chem. 1985, 50, 3940.
21. Unpublished results of research conducted at UCSB by Drs. L. Van Hijfte and K. D. Moeller. The X-ray crystallography was carried out by Professor J. L. Petersen of West Virginia University. Recently, Professor Raymond Funk disclosed the results of studies which also led to the formation of a transfused system: Funk, R. L.; Bolton, G. L.; Umstead, Daggett, J.; Hansen, M. M.; Horcher, L. H. M. Tetrahedron 1985, 41, 3479.
22. Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Antibiot. 1980, 33, 4365. Danishefsky, S.; Zamboni, R.; Kahn, M.; Etheredge, S. J. J. Am. Chem. Soc. 1980, 102, 2097. Danishefsky, S.; Zamboni, R. Tetrahedron Lett. 1980, 21, 3439. Danishefsky, S.; Zamboni, R.; Kahn, M.; Etheredge, S. J. J. Am. Chem. Soc. 1981, 103, 3460. Shibasaki, K.; Iseki, K.; Ikegami, S. Tetrahedron Lett. 1980, 21, 2587. Iseki, K.; Yamazaki, M.; Shibasaki, M.; Ikegami, S. Tetrahedron 1981, 37, 4411. Tatsuta, K.; Akimoto, K.; Kinoshita, M. Tetrahedron 1981, 37, 4365. Mehta, G.; Reddy, A. V.; Murthy, A. N.; Reddy, D. S. J. Chem. Soc., Chem. Commun. 1982, 540. Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1983, 24, 5325. Schuda, P. F.; Heimann, M. R. Tetrahedron Lett. 1983, 24, 4267. Funk, R. L.; Bolton, G. L. Abstracts of Papers, 189th American Chemical Society National Meeting, Miami Beach, FL; American Chemical Society: Washington, DC, 1985; ORGN 0085. Koreeda, M.; Mislankar, S. G. J. Am. Chem. Soc. 1983, 105, 7203. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1981, 103, 7380. Demuth, M.; Ritterskamp, P.; Schaffner, K. Helv. Chim. Acta 1984, 67, 2023. Exon, C.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 2477. Ito, T.; Tomiyoshi, N.; Nakamura, K.; Azuma, S.; Izawa, M.; Maruyama, F.; Yanagiya, M.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1982, 1721. Demuth, M.; Ritterskamp, P.; Weigt, E.; Schaffner, K. J. Am. Chem. Soc. 1986, 108, 4149 Mehta, G.; Murthy, A. N.; Reddy, A. S.; Reddy, A. V. J. Am. Chem. Soc. 1986, 108, 3443.
23. Unpublished results of research conducted at UCSB by Dr. Luc Van Hijfte. Current address: Department of Organic Chemistry, The State University of Gent, Gent, Belgium. For a reference to hypnophilin see: Kupka, J.; Anke, T.; Giannetti, B.; Steglich, W. Arch. Microbiol. 1981, 130, 223.
24. Unpublished research conducted at University of California—Santa Barbara by Mr. Onorato Campopiano.
25. Campopiano, O.; Little, R. d.; Petersen, J. L. J. Am. Chem. Soc. 1985, 107, 3721.
26. Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, Chapter 4.
27. Moeller, K. D.; Little, R. D. Tetrahedron Lett. 1985, 26, 3417. (b) Unpublished research conducted at UCSB by Mr. Charles Billera. See also: Moeller, K. D. Ph.D. Dissertation, UCSB, 1985, unpublished results.
28. Little, R. D.; Bode, H.; Stone, K. J.; Wallquist, O.; Dannecker, R. J. Org. Chem. 1985, 50, 2400. (b) Weinreb, S. M.; Staib, R. R. Tetrahedron 1982, 38, (Report No. 136), 3087. Fallis, A. G. Can. J. Chem. 1984, 62, 183. Ciganek, E. In Organic Reactions; Wiley: New York, 1984; Vol. 32, Chapter 1.
29. Unpublished research conducted at University of California—Santa Barbara with Mr. Mohamed Masjadezedeh.