Acetylenic vinyllithiums: Consecutive cycloisomerization-[4 + 2] cycloaddition reactions

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8216-8228

  Bailey, William F ^a   Wachter Jurcsak, Nanette M ^a,c   Pineau, Mark R ^a   Ovaska, Timo V ^b   Warren, Rachel R ^b   Lewis, Carl E ^b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b The Department of Government and International Relations   (United States)

^c HOFSTRA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000743156     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961437l     Document Type: Article

References (78)

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27. It should be noted that, although the ring closure of an olefinic or acetylenic organolithium is often termed an anionic cyclization, the lithium atom is intimately involved in the process and undoubtedly serves to facilitate the cyclization. For a discussion of the unique role of lithium in the cyclization of 5-hexenylalkalies, see: Bailey, W. F.; Punzalan, E. R. J. Am. Chem. Soc. 1994, 116, 6577.
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32. (e) Intramolecular addition of stabilized carbanions to alkoxyacetylenes have also been reported: Funk, R. L.; Bolton, G. L.; Brummond, K. M.; Elleatad. K. E.; Stallman, J. B. J. Am. Chem. Soc. 1993, 115, 7023.
33. Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080.
34. A preliminary account of this investigation has appeared, see: Ovaska, T. V.; Warren, R. R.; Lewis, C. E.; Wachter-Jurcsak, N. M.; Bailey, W. F. J. Org. Chem. 1994, 59, 5868.
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43. See, for example: (a) Bailey, W. J.; Golden, H. R. J. Am. Chem. Soc. 1953, 75, 4780. (b) Bailey, W. J.; Sorenson, W. R. J. Am. Chem. Soc. 1954, 76, 5421. (c) Bloomquist, A. T.; Wolinsky, J.; Meinwald, Y. C.; Congone, D. T. J. Am. Chem. Soc. 1956, 78, 6075. (d) van Straten, J. W.; van Norden, J. J.; van Schaik, T. A. M.; Franke, C. T.; de Wolf, W. N.; Bichelhaupt, F. Rec. Trav. Chim. Pays-Bas. 1978, 97, 105.
44. See, for example: (a) Bailey, W. J.; Golden, H. R. J. Am. Chem. Soc. 1953, 75, 4780. (b) Bailey, W. J.; Sorenson, W. R. J. Am. Chem. Soc. 1954, 76, 5421. (c) Bloomquist, A. T.; Wolinsky, J.; Meinwald, Y. C.; Congone, D. T. J. Am. Chem. Soc. 1956, 78, 6075. (d) van Straten, J. W.; van Norden, J. J.; van Schaik, T. A. M.; Franke, C. T.; de Wolf, W. N.; Bichelhaupt, F. Rec. Trav. Chim. Pays-Bas. 1978, 97, 105.
45. See, for example: (a) Bailey, W. J.; Golden, H. R. J. Am. Chem. Soc. 1953, 75, 4780. (b) Bailey, W. J.; Sorenson, W. R. J. Am. Chem. Soc. 1954, 76, 5421. (c) Bloomquist, A. T.; Wolinsky, J.; Meinwald, Y. C.; Congone, D. T. J. Am. Chem. Soc. 1956, 78, 6075. (d) van Straten, J. W.; van Norden, J. J.; van Schaik, T. A. M.; Franke, C. T.; de Wolf, W. N.; Bichelhaupt, F. Rec. Trav. Chim. Pays-Bas. 1978, 97, 105.
46. See, for example: (a) Bailey, W. J.; Golden, H. R. J. Am. Chem. Soc. 1953, 75, 4780. (b) Bailey, W. J.; Sorenson, W. R. J. Am. Chem. Soc. 1954, 76, 5421. (c) Bloomquist, A. T.; Wolinsky, J.; Meinwald, Y. C.; Congone, D. T. J. Am. Chem. Soc. 1956, 78, 6075. (d) van Straten, J. W.; van Norden, J. J.; van Schaik, T. A. M.; Franke, C. T.; de Wolf, W. N.; Bichelhaupt, F. Rec. Trav. Chim. Pays-Bas. 1978, 97, 105.
47. The vast primary literature on the Diela-Alder reaction has spawned an extensive number of reviews. A representative selection of monographs may be found in: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994. (b) March, J. A. Advanced Organic Chemistry, 4th ed.; Wiley Interscience: New York, 1992; pp 839-852. (c) Holmes, H. L. Org. React. 1958, 4, 60.
48. The vast primary literature on the Diela-Alder reaction has spawned an extensive number of reviews. A representative selection of monographs may be found in: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994. (b) March, J. A. Advanced Organic Chemistry, 4th ed.; Wiley Interscience: New York, 1992; pp 839-852. (c) Holmes, H. L. Org. React. 1958, 4, 60.
49. The vast primary literature on the Diela-Alder reaction has spawned an extensive number of reviews. A representative selection of monographs may be found in: (a) Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994. (b) March, J. A. Advanced Organic Chemistry, 4th ed.; Wiley Interscience: New York, 1992; pp 839-852. (c) Holmes, H. L. Org. React. 1958, 4, 60.
50. Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: Amsterdam, 1988.
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54. 15
55. Bailey, W. F.; Ovaska, T. V. Organometallics 1990, 9, 1694.
56. For reviews of the preparation and reactions of conjugated allenenes, see: (a) Lander, P. D. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: New York, 1982; Vol. 1, pp 205-222. (b) Hopf, H. Ibid. Vol. 2, pp 563-576.
57. For reviews of the preparation and reactions of conjugated allenenes, see: (a) Lander, P. D. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: New York, 1982; Vol. 1, pp 205-222. (b) Hopf, H. Ibid. Vol. 2, pp 563-576.
58. The preparation of alkenylidenecycloalkanes by cyclization of acetylenic alkyllithiums bearing a propargylic leaving group has been described: see, Bailey, W. F.; Aspris, P. H. J. Org. Chem. 1995, 60, 754.
59. (a) Full details are available in the Ph.D. Dissertation of Nanette M. Wachter-Jurcsak, University of Connecticut, Storrs, CT, 1995.
60. -1. Crystallographic data for 16 appear in footnote 14 of ref 8. The structures were solved by direct methods. The authors have deposited atomic coordinates for 15 and 16 with the Cambridge Crystallographic Data Center. The coordinates may be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
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