Bond Fixation in Annulenes. 9. Equalization of Ring Inversion and Bond Shifting Energetics in 1,2,3,4-Tetramethylcyclooctatetraene. Asymmetric Synthesis, Direct Resolution, and Absolute Configuration of the Optically Active Hydrocarbon

Journal of the American Chemical Society

Volumn 102, Issue 15, 1980, Pages 5026-5032

  Paquette, Leo A ^a   Gardlik, John M ^a   Johnson, Larry K ^a   McCullough, Kevin J ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3242837192     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00535a033     Document Type: Article

References (24)

1. For part 8, see: Paquette, L. A.; Gardlik, J. M. J. Am. Chem. Soc., preceding paper in this issue.
2. The Ohio State University Dissertation Fellow, 1977-1978.
3. NATO Postdoctoral Fellow of the Science Research Council, 1978-1980.
4. Allinger, N. L.; Sprague, J. T.; Finder, C. J. Tetrahedron 1973, 29, 2519.
5. Anet, F. A. L. J. Am. Chem. Soc. 1962, 84, 671.
6. Anet, F. A. L.; Bourn, A. J. R.; Lin, Y. S. J. Am. Chem. Soc. 1964, 86, 3576.
7. Oth, J. F. M.; Merenyi, R.; Martini, Th.; Schroder, G. Tetrahedron Lett. 1966, 3087.
8. Gwynn, D. E.; Whitesides, G. M.; Roberts, J. D. J. Am. Chem. Soc. 1965, 87, 2862.
9. Buchanan, G. W. Tetrahedron Lett. 1972, 665.
10. Luz, Z.; Meiboom, S. J. Chem. Phys. 1973, 59, 1077.
11. Dewar, M. J. S.; Harget, A.; Haselbach, E. J. Am. Chem. Soc. 1969, 91, 7521.
12. Paquette, L. A.; Gardlik, J. M.; Photis, J. M. J. Am. Chem. Soc.(8) Preliminary reports on the two methods of resolution employed have previously appeared: (a) Gardlik, J. M.; Johnson, L. K.; Paquette, L. A.; Solheim, B. A.; Springer, J. P.; Clardy, J. J. Am. Chem. Soc., 1979,101, 1615.
13. Gardlik, J. M.; Paquette, L. A., Tetrahedron Lett. 1979, 3597. 1976, 98, 7096
14. For a preliminary communication on this subject, consult: Gardlik, J. M.; Paquette, L. A.; Gleiter, R. J. Am. Chem. Soc., 1979, 101, 1617.
15. Paquette, L. A.; Photis, J. M.; Ewing, G. D. J. Am. Chem. Soc. 1975, 97, 3538.
16. Paquette, L. A.; Photis, J. M. J. Am. Chem. Soc. 1976, 98, 4936.
17. Huang, W.-Y.; Holmes, H. L.; Fieser, L. F. J. Am. Chem. Soc. 1952, 74, 5920.
18. Photis, J. M. Ph.D. Dissertation, The Ohio State University, 1975.
19. Allinger, N. L., private communication. The entropy difference between this pair of bond-shift isomers is O.
20. The NMR spectrum of this dianion recorded in ND3 solution at-55 °C is illustrated in ref 10a 15) See, for example, Chase, B. H.; Hey, D. H. J. Chem. Soc. 1952, 554. Bardhan, J. C. private communication. 1928, 2604. Turner, D. L.; Bhattacharyya, B. K.; Graber, R. P.; Johnson, W. S. J. Am. Chem. Soc. 1958, 72, 5654. Cason, J. J. Org. Chem. 1948, 13, 227. Stallberger-Stenhagen, S. J. Am. Chem. Soc. 1947, 69, 2568.
21. Corey, E. J.; Sachdev, H. S. J. Org. Chem. 1975, 40, 579.
22. Doehner, R.; Jenkins, J., unpublished observations in this laboratory.
23. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384. We thank Professor Pirkle for providing us with a sample of 22* which enabled the feasibility studies to be made. Larger quantities of 22* were purchased from the Aldrich Chemical Co.
24. Paquette, L. A.; Gardlik, J. M. J. Am. Chem. Soc., accompanying paper in this issue