Three-electron S(N)2 reactions of arylcyclopropane cation radicals. 2. Steric and electronic effects of substitution

Journal of the American Chemical Society

Volumn 119, Issue 5, 1997, Pages 994-1004

  Dinnocenzo, J P ^a   Zuilhof, H ^a   Lieberman, D R ^a   Simpson, T R ^a   McKechney, M W ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; PHOTOCHEMISTRY; REACTION ANALYSIS; SPECTROPHOTOMETRY; STEREOCHEMISTRY;

EID: 0031035024     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja963112s     Document Type: Article

References (65)

1. (a) Taken in part from the doctoral thesis of T.R.S., University of Rochester, 1995.
2. (b) A preliminary account of this work has been published: Dinnocenzo, J. P.; Lieberman, D. R.; Simpson, T. R. J. Am. Chem. Soc. 1993, 115, 366.
3. Dinnocenzo, J. P.; Simpson, T. R.; Zuilhof, H.; Todd, W P.; Heinrich, T. Preceding paper in this issue (J. Am. Chem. Soc. 1997, 119, 987.
4. Rao, V. R.; Hixson, S. S. J. Am. Chem. Soc. 1979, 101, 6458.
5. (a) Casey, C. P.; Polichnowski, S. W.; Shusterman, A. J.; Jones, C. R. J. Am. Chem. Soc. 1979, 101, 7282.
6. (b) In our hands the reaction yielded between 0 and 26%. In general, we have found other procedures to be somewhat more reproducible: Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215.
7. Olofson, R. A.; Dougherty, C. M. J. Am. Chem. Soc. 1973, 95, 581.
8. Baron, W. J.; Hendrick, M. E.; Jones, M., Jr. J. Am. Chem. Soc. 1973, 95, 6286.
9. (a) S = MeO, Me: Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
10. (b) S = F, Cl: Denmark, S. E.; Edwards, J. P. J. Org. Chem. 1991, 56, 6974.
11. (c) S = C(=O)Me: Levina, R. Ya.; Gembitskii, P. A.; Kostin, V. N.; Shostakovskii, S. M.; Treshchova, E. G. Zh. Obshch. Khim. 1963, 33, 365.
12. (d) S = OC(=O)Me: Horrom, B. W.; Mazdiyasni, H. OPPI Briefs 1992, 6, 696.
13. See preceding paper in this issue (J. Am. Chem. Soc. 1997, 119, 987) for general description of the reaction procedure.
14. Tamelen, E. E. van; Rudler, H.; Bjorkland, C. J. Am. Chem. Soc. 1971, 93, 7113.
15. Arnold, D. R.; Hinman, R. L.; Glick, A. H. Tetrahedron Lett. 1964, 5, 1425.
16. (a) Todd, W. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R. J. Am. Chem. Soc. 1991, 113, 3601.
17. (b) Dockery, K. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P. J. Am. Chem. Soc. 1997, 119. In press.
18. +: Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
19. α: Wayner, D. D. M.; Arnold, D. R. Can J. Chem. 1984, 62, 1164.
20. + (COMe) is a calculated value (see ref 12a).
21. (a) Sunko, D. E.; Hehre, W. J. Prog. Phys. Org. Chem. 1983, 14, 205.
22. (b) Lee, I. Chem. Soc. Rev. 1995, 24, 223.
23. For other examples of this technique to determine kinetic isotope effects, see: (a) De Vaal, P.; Lodder, G.; Cornelisse, J. J. Phys. Org. Chem. 1992, 5, 581.
24. (b) Zuilhof, H.; Van Gelderen, F. A.; Cornelisse, J., Lodder, G. Submitted for publication.
25. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
26. (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
27. Zuilhof, H.; Dinnocenzo, J. P.; Reddy, C.; Shaik, S. J. Phys. Chem. 1996, 100, 15774.
28. Hudson, C. E.; Giam, C. S.; McAdoo, D. J. J. Org. Chem. 1993, 58, 2017.
29. Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287.
30. ox(N), were obtained from the equilibrium constants for electron transfer between reference aromatic compounds and the cyclopropanes as studied by picosecond laser flash transient absorption spectroscopy (Lingenfelter, T. G.; Simpson, T. R.; Dinnocenzo, J. P. Manuscript in preparation).
31. 20b
32. 20d was used for 8.
33. (a) Doering, W. v. E. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 5279.
34. (b) McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
35. (c) Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. In Gas-Phase Ion and Neutral Thermochemistry; Lide, D. R. J., Ed.; J. Phys. Chem. Ref. Data 1988, 17, Supplement no. 1.
36. (c) Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. In Gas-Phase Ion and Neutral Thermochemistry; Lide, D. R. J., Ed.; J. Phys. Chem. Ref. Data 1988, 17, Supplement no. 1.
37. (d) Wayner, D. D. M.; McPhee, D. J.; Griller, D. J. Am. Chem. Soc. 1988, 110, 132.
38. (e) Wayner, D. D. M., personal communication.
39. (a) AM1: Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart. J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
40. (b) PM3: Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221.
41. (a) Dauben, W. G.; Chitwood, J. L. J. Am. Chem. Soc. 1968, 90, 6876.
42. (b) Ando, T.; Morisaki, H. Tetrahedron Lett. 1979, 20, 121.
43. (c) Shiner, V. J., Jr.; Reib, R. C. Tetrahedron Lett. 1979, 20, 121.
44. (d) Shiner, V. J., Jr.; Tai, J. J. J. Am. Chem. Soc. 1981, 103, 436.
45. (e) Yamataka, H.; Ando, T. J. Am. Chem. Soc. 1982, 104, 1808.
46. (e) Yamataka, Y.; Ando, T.; Nagase, S.; Hanamura, M.; Morokuma, K. J. Org. Chem. 1984, 49, 631.
47. (a) Adam W.; Walter, H.; Chen, G.-F.; Williams, F. J. Am. Chem. Soc. 1992, 114, 3007.
48. (b) Weng, H.; Sheik, Q.; Roth, H. D. J. Am. Chem. Soc. 1995, 117, 10655.
49. (a) Zona, T. A.; Goodman, J. L. J. Am. Chem. Soc. 1993, 115, 4925.
50. (b) Arnold, D. R.; Du, X. Can. J. Chem. 1994, 72, 403.
51. (c) ref. 23b.
52. Streitwieser, A. Solvolytic Displacement Reactions; McGraw-Hill: New York, 1962; p 13.
53. Krogh-Jespersen, K.; Roth, H. D. J. Am. Chem. Soc. 1992, 114, 8388, and references therein.
54. Shaik, S.; Reddy, A. C.; Ioffe, A.; Dinnocenzo, J. P.; Danovich, D.; Cho, J. K. J. Am. Chem. Soc. 1995, 117, 3205.
55. Shaik, S. S.; Dinnocenzo, J. P. J. Org. Chem. 1990, 55, 3434.
56. Simes, B. E.; Rickborn, B.; Fluornoy, J. M. Berlman, I. B. J. Org. Chem. 1988, 53, 4613.
57. Johnson, S. A.; Hunt, H. R.; Neumann, H. M. Inorg. Chem. 1963, 2, 960.
58. (a) Miller, J. B. J. Org. Chem. 1959, 24, 560.
59. (b) Smith, L. I.; Howard, K. L. Organic Synthesis Wiley: New York, 1959; Collect Vol. 3, p 351.
60. Walborsky, H. M.; Murari, M. P. Can. J. Chem. 1984, 62, 2464.
61. (a) Pretch, E.; Clerc, T.; Seibl, J.; Simon, W. Tables of Spectral Data for Structure Determination of Organic Compounds; Springer-Verlag: Berlin, 1983; p I-190.
62. (b) Socrates, G. Infrared Characteristic Group Frequencies, Wiley-Interscience: Chichester, 1980; p 55.
63. Meyers, A. I.; Ritter, J. J. J. Org. Chem. 1958, 23, 1918.
64. MOPAC93; Dr. J. J. P. Stewart & Fujitsu Ltd., Tokyo, 1993.
65. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petterson, G. A.; Montgomery, J. A.; Raghavari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Repogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 94, versions C.3 & D.1; Gaussian, Inc.: Pittsburgh, PA, 1995.