Cyclopropanes. XXV. The Cyclopropyl Anion

Journal of the American Chemical Society

Volumn 92, Issue 8, 1970, Pages 2445-2450

  Walborsky, H M ^a   Motes, John M ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001505175     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00711a040     Document Type: Article

References (29)

1. D. J. Cram, “Fundamentals of Carbanion Chemistry,” Academic Press, New York, N. Y., 1965.
2. H. M. Walborsky, F. J. Impastato, and A. E. Young, J. Amer. Chem. Soc., 86, 3283 (1964).
3. J. B. Pierce and H. M. Walborsky, J. Org. Chem., 33, 1962 (1968).
4. H. M. Walborsky and F. M. Hornyak, J. Amer. Chem. Soc., 77, 6026 (1955).
5. H. M. Walborsky, A. A. Youssef, and J. M. Motes, J. Amer. Chem. Soc., 84, 2465 (1962).
6. H. M. Walborsky and C. G. Pitt, J. Amer. Chem. Soc., 84, 4831 (1962).
7. D. J. Cram, C. A. Kingsbury, and B. Rickborn, J. Amer. Chem. Soc., 83, 3688 (1961).
8. D. J. Cram, B. Rickborn, C. A. Kingsbury, and P. Haberfield, J. Amer. Chem. Soc., 83, 3678 (1961);
9. D. J. Cram and P. Haberfield, J. Amer. Chem. Soc., 83, 2354 (1961).
10. H. C. Brown, R. S. Fletcher, and R. B. Johannesen, J. Amer. Chem. Soc., 73, 212 (1951);
11. H. C. Brown and M. Borkowski, J. Amer. Chem. Soc., 74, 1894 (1952).
12. H. M. Walborsky, Rec. Chem. Progr., 23, 75 (1962).
13. For a review see, M. Y. Lukina, Russ. Chem. Rev., 31, 419 (1962).
14. R. Stewart, J. P. O'Donnell, D. J. Cram, and B. Rickborn, Tetrahedron, 18, 317 (1962).
15. R. G. Pearson and R. L. Dillon, J. Amer. Chem. Soc., 75, 2439 (1955).
16. G. S. Hammond, J. Amer. Chem. Soc., 77, 334 (1955).
17. H. Zimmerman, Angew. Chem. Intern. Ed. Engl., 3, 157 (1964).
18. L. Melander, “Isotope Effects on Reaction Rates,” Ronald Press Co., New York, N. Y., 1960.
19. C. G. Swain, E. C. Stivers, J. F. Reuwer, Jr., and L. J. Schaad, J. Amer. Chem. Soc., 80, 5885 (1958).
20. T ≈ 2-3 is usually observed in reactions that appear to involve bond breaking in the rate-determining step; see A. I. Shatenshtein, Tetrahedron, 18, 95 (1962) and
21. A. Streitwieser and D. E. Von Sickle, J. Amer. Chem. Soc., 82, 1513 (1960).
22. D. J. Cram, D. A. Scott, and W. D. Nielsen, J. Amer. Chem. Soc., 83, 3696 (1961).
23. W. T. Van Wijnen, M. Van Wijnen, H. Sternberg, and T. J. De Boer, Tetrahedron, 23, 3763 (1967).
24. A. Streitwieser, Jr., L. Verbit, and P. Stang, J. Org. Chem., 29, 3706 (1964).
25. L. C. Leitch, et al., Can. J. Chem., 35, 345 (1957).
26. W. H. Washburn and M. J. Mahoney, J. Amer. Chem. Soc., 80, 504 (1958).
27. Deuterium analyses by combustion method were performed by J. Nemeth, Urbana, Ill.
28. E. Bergmann, J. Chem. Soc., 412 (1936);
29. M. L. Sykes, M. S. Thesis, Florida State University, 1958.