Synthesis and Solvolysis of syn- and anti-(6-Oxabicyclo[3.1.0]hex-3-yl)methyl p-Bromobenzenesulfonates

Journal of Organic Chemistry

Volumn 46, Issue 17, 1981, Pages 3512-3519

  David, Feeya ^a  

^a UNIVERSITY OF BRASILIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000406679     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00330a027     Document Type: Article

References (55)

1. A preliminary account of this work has been published: David, F. J. Chem. Soc., Chem. Commun. 1979, 553.
2. Peters, E. N. J. Org. Chem. 1978, 43, 4006.
3. Whalen, D. L.; Brown, S.; Ross, A. M.; Russel, H. M. J. Org. Chem. 1978, 43, 428.
4. Whalen, D. L.; Cooper, J. D. J. Org. Chem. 1978, 43, 432.
5. Santelli, M.; Viala, J. Tetrahedron 1978, 34, 2327.
6. Santelli, M. J. Chem. Soc. C 1974, 214.
7. Danen, J. C. J. Am. Chem. Soc. 1972, 94, 4835.
8. Morita, H.; Oae, S. Tetrahedron Lett. 1969, 1347.
9. Richey, H. G., Jr.; Kinsman, D. V. Tetrahedron Lett. 1969, 2505.
10. Padwa, A.; Das, N. C.; Eastman, D. J. Am. Chem. Soc. 1969, 91, 5178.
11. For recent reviews and references, see: (a) Wiberg, K. B.; Hess, B. A.; Ashe, A. J. “Carbonium Ions”; Olah, G. A., Schleyer, P.V.R., Eds.; Wiley: New York, 1972; Vol. III, Chapter 26.
12. Richey. H. G., Jr. Carbonium Ions., 1972; Chapter 25.
13. Brown, H. C.; Rao, C. G.; Ravindanathan, M. J. Am. Chem. Soc. 1977, 99, 7663 and references cited therein.
14. Walsh, A. D. Trans. Faraday Soc. 1949, 45, 179.
15. References 3b and 4a.
16. Waters, W. A. J. Chem. Soc. 1933, 1551
17. Hornback, J. M. J. Org. Chem. 1973, 38, 4122.
18. Murdock, K. C.; Angier, R. B. J. Org. Chem. 1962, 27, 2395.
19. Schmid, G. H.; Wolkoff, A. W. J. Org. Chem. 1967, 32, 254.
20. The exo configuration of the product 6a is a necessary consequence of an intramolecular displacement reaction that effects cyclization.
21. See Experimental Section.
22. Meinwald, J.; Crandall, J.; Hym, W. E. Org. Synth. 1965, 45, 77.
23. Brown, H. C. “Hydroboration”; W. A. Benjamin, Inc.: New York, 1962.
24. Winstein, S.; Sonnenberg, J. J. Am. Chem. Soc. 1961, 83, 3244.
25. Tipson, R. S. J. Org. Chem. 1946, 11, 235
26. The solvolysis rate for compound 9 was determined by spectrophotometric using the ampule technique.
27. The rest remained unidentified.
28. Capon, B. Q. Rev., Chem. Soc. 1964, 18, 45.
29. Winstein, S.; Grundwald, E.; Ingraham, L.L. J. Am. Chem. Soc. 1948, 70, 821.
30. Paquette, L. A.; Dunkin, I. R.; Freeman, J. P.; Storn, P. C. J. Am. Chem. Soc. 1972, 94, 8124.
31. Spurlock, L. A.; Fayter, R. G. J. Am. Chem. Soc. 1972, 94, 2707.
32. Amatavivadhana, F. Ph.D. Thesis, Ohio University, 1971.
33. Raaen, V. F.; Juhlke, T.; Brown, F. J.; Collins, C. J. J. Am. Chem. Soc. 1974, 96, 5928.
34. Shiner, V. J., Jr. J. Am. Chem. Soc. 1974, 96, 6187.
35. Sunko, D. E.; Bordé, S. “Isotope Effects in Chemical Reactions”; Collin, C. J., Bowman, N. S., Eds.; ACS Monograph No. 167; Van Nostrand Reinhold: New York, 1970; Chapter 3.
36. Humski, H.; Malojcic, R.; Bordé, S.; Sunko, D. E. J. Am. Chem. Soc. 1970, 92, 6534.
37. This magnitude was analyzed and criticized as incorrect, see: Maskill, H. J. Am. Chem. Soc. Soc. 1976, 98, 8482.
38. Murr, B. L.; Conkling, T. A. J. Chem. Soc. 1970, 92, 3464.
39. Lee, C. C.; Wong, W. C. Can. J. Chem. 1965, 42, 2254.
40. In the S-l process, the magnitude of the α-deuterium isotope effect changes significantly with the leaving group while a slight change (1-2% per deuterium atom) was observed with a change in solvent. For the SN2 mechanism the effect of leaving group of the α-deuterium effect is similar to that in the Sl mechanism but over a much smaller range. See: Shiner, V. J., Jr.; Rapp, M. W.; Pinnick, H. R. J. Am. Chem. Soc. 1970, 92, 232; ref 25b.
41. Shiner, V. J., Jr.; Fisher, R. D.; Dowd, W. J. J. Am. Chem. Soc. 1969, 91, 7748.
42. I thank one of the referees for his comments on this point.
43. One could argue that the small α-deuterium isotope effect of 5c might result from the solvent-assisted reaction. However, the complete absence of formation of substitution products in the solvolysis of 3c does not favotr this argument.
44. Allred, E. L.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 3991, 3998, 4012.
45. References 29a, pp 177-181.
46. Streitwieser, A., Jr.; Waiss, A. C. J. Org. Chem. 1962, 27, 290.
47. Weiner, H.; Sucem, R. A. J. Am. Chem. Soc. 1965, 87, 287, 292.
48. Streitwieser, A., Jr.; Walsh, T. D.; Wolfe, J. R. J. Am. Chem. Soc. 1965, 87, 3682.
49. Fieser, L.; Fieser, M. “Reagents for Organic Chemistry”; John-Wiley: New York, 1967.
50. Perrin, P. P.; Armarego, L. F.; Perrin, D. R. “Purification of Laboratory Chemicals”; Pergamon Press: New York, 1966.
51. Hess, H. M.; Brown, H. C. J. Org. Chem. 1967, 32, 4138.
52. The butyllithium solution was sure-sealed (Aldrich, 1.6 M). The reaction mixture was kept below-60 °C all the time.
53. Buddenbaum, W. E. Ph.D. Thesis, Indiana University, 1964.
54. Swain, C. G.; Morgan, C. R. J. Org. Chem. 1964, 29, 2097.
55. The program was written by W. E. Buddenbaum and modified by J. G. Jewett.