Charge distribution and charge separation in radical rearrangement reactions

Advances in Physical Organic Chemistry

Volumn 38, Issue , 2003, Pages 111-130

  Zipse, H ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842798666     PISSN: 00653160     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-3160(03)38003-7     Document Type: Review

References (90)

1. K.N. Houk J. Gonzalez Y. Li Acc. Chem. Res. 28 1995 81
2. M.J.S. Dewar C. Jie Acc. Chem. Res. 25 1992 537
3. A.L.J. Beckwith D. Crich P.J. Duggan Q. Yao Chem. Rev. 97 1997 3273
4. S. Saebo A.L.J. Beckwith L. Radom J. Am. Chem. Soc. 106 1984 5119
5. P.S. Skell J.G. Traynham Acc. Chem. Res. 17 1984 160
6. (a) A.C. Hopkinson M.H. Lieu I.G. Csizmadia Chem. Phys. Lett. 71 1980 557
7. (b) T. Hoz M. Sprecher H. Basch J. Phys. Chem. 89 1985 1664
8. (c) B. Engels S.D. Peyerimhoff P.S. Skell J. Phys. Chem. 94 1990 1267
9. (d) M. Guerra J. Am. Chem. Soc. 114 1992 2077
10. (e) H. Ihee A.H. Zewail W.A. Goddard III J. Phys. Chem. A 103 1999 6638
11. (f) X. Zheng D.L. Phillips J. Phys. Chem. A 104 2000 1030
12. (g) P. Brana B. Menendez T. Fernandez J.A. Sordo J. Phys. Chem. A 104 2000 10842
13. (h) Z.-H. Li K.-N. Fan M.W. Wong J. Phys. Chem. A 105 2001 10890
14. (i) H. Ihee J. Kua W.A. Goddard III A.H. Zewail J. Phys. Chem. A 105 2001 3623
15. B. Neumann H. Zipse Org. Biomol. Chem. 1 2003 168
16. Zipse, H., unpublished results.
17. A.E. Reed L.A. Curtiss F. Weinhold Chem. Rev. 88 1988 899
18. B. Engels S.D. Peyerimhoff J. Mol. Struct. 138 1986 59
19. J. Cao H. Ihee A.H. Zewail Proc. Natl Acad. Sci. USA 96 1999 338
20. H. Ihee V.A. Lobastov U. Gomez B.M. Goodson R. Srinivasan C.-Y. Ruan A.H. Zewail Science 291 2001 458
21. (a) R.A. More O'Ferrall J. Chem. Soc. 1970 274
22. (b) W.P. Jencks Chem. Rev. 72 1972 706
23. All charge and spin density values mentioned in this account have been calculated using the Natural Population Analysis scheme and the Becke3LYP hybrid functional as implementation in gaussian 98, Rev. A.11, together with the pruned ultrafine grid of 99 radial shells and 590 angular points per atom as well as a tight conversion criterion. All values are given in atomic units.
24. (a) E.W. Tan J.P. Shaw J. Org. Chem. 61 1996 5635
25. (b) E.W. Tan B. Chan A.G. Blackman J. Am. Chem. Soc. 124 2002 2078
26. F.L. Cozens M. O'Neill R. Bogdanova N. Schepp J. Am. Chem. Soc. 116 1997 10652
27. (a) H. Zipse J. Chem. Soc. Perkin Trans. 2 1996 1797
28. (b) H. Zipse J. Am. Chem. Soc. 119 1997 1087
29. (c) H. Zipse M. Bootz J. Chem. Soc. Perkin Trans. 2 2001 1566
30. (a) A.L.J. Beckwith P.L. Tindal Aust. J. Chem. 24 1971 2099
31. (b) M.J. Perkins B.P.J. Roberts J. Chem. Soc. Perkin Trans. 2 1975 77
32. L.R.C. Barclay D. Griller K.U. Ingold J. Am. Chem. Soc. 104 1982 4399
33. P. Kocovsky I. Stary F. Turecek Tetrahedron Lett. 27 1986 1513
34. H.-G. Korth R. Sustmann K.S. Gröninger M. Leising B. Giese J. Org. Chem. 53 1988 4364
35. A.L.J. Beckwith P.J. Duggan J. Chem. Soc. Perkin Trans. 2 1992 1777
36. A.L.J. Beckwith P.J. Duggan J. Chem. Soc. Perkin Trans. 2 1993 1673
37. D. Crich G.F. Filzen J. Org. Chem. 60 1995 4834
38. A.L.J. Beckwith P.J. Duggan J. Am. Chem. Soc. 118 1996 12838
39. H. Zipse Acc. Chem. Res. 32 1999 571
40. E. Lancote P. Renaud Angew. Chem. 110 1998 2369 Angew. Chem. Int. Ed. 1998, 37 , 2259
41. L.R.C. Barclay J. Lusztyk K.U. Ingold J. Am. Chem. Soc. 106 1984 1793
42. W. Knapp-Pogozelski T.D. Tullius Chem. Rev. 98 1998 1089
43. A.P. Breen J.A. Murphy Free Rad. Biol. Med. 18 1995 1032
44. (a) M. Dizdaroglu C. von Sonntag D. Schulte-Frohlinde J. Am. Chem. Soc. 97 1975 2277
45. (b) G. Behrens G. Koltzenburg A. Ritter D. Schulte-Frohlinde Int. J. Rad. Biol. 33 1978 163
46. (c) G. Koltzenburg G. Behrens D. Schulte-Frohlinde J. Am. Chem. Soc. 104 1982 7311
47. (a) R. Glatthaar M. Spichty A. Gugger R. Batra W. Damm M. Mohr H. Zipse B. Giese Tetrahedron 56 2000 4117
48. (b) E. Meggers A. Dussy T. Schäfer B. Giese Chem. Eur. J. 6 2000 485
49. (c) A. Gugger R. Batra P. Rzadek G. Rist B. Giese J. Am. Chem. Soc. 119 1997 8740
50. (d) B. Giese X. Beyrich-Graf P. Erdmann M. Petretta U. Schwitter Chem. Biol. 2 1995 367
51. (e) B. Giese X. Beyrich-Graf J. Burger C. Kesselheim M. Senn T. Schäfer Angew. Chem. Int. Ed. Engl. 32 1993 1742
52. (a) M. Newcomb N. Miranda M. Sannigrahi X. Huang D. Crich J. Am. Chem. Soc. 123 2001 6445
53. (b) J.H. Horner M. Newcomb J. Am. Chem. Soc. 123 2001 4364
54. (c) B.C. Bales J.H. Horner X. Huang M. Newcomb D. Crich M.M. Greenberg J. Am. Chem. Soc. 123 2001 3623
55. (d) M. Newcomb N. Miranda X. Huang D. Crich J. Am. Chem. Soc. 122 2000 6128
56. (e) P.O. Whitted J.A. Horner M. Newcomb X. Huang D. Crich Org. Lett. 1 1999 153
57. (f) M. Newcomb J.H. Horner P.O. Whitted D. Crich X. Huang Q. Yao H. Zipse J. Am. Chem. Soc. 121 1999 10685
58. (g) S.-Y. Choi D. Crich J.H. Horner X. Huang F.N. Martinez M. Newcomb D.J. Wink Q. Yao J. Am. Chem. Soc. 120 1998 211
59. (a) D. Crich K. Ranganathan J. Am. Chem. Soc. 124 2002 12422
60. (b) D. Crich S. Neelamkavil Org. Lett. 4 2002 2573
61. (c) D. Crich K. Ranganathan X. Huang Org. Lett. 3 2001 1917
62. (d) D. Crich X. Huang M. Newcomb J. Org. Chem. 65 2000 523
63. (e) D. Crich X. Huang M. Newcomb Org. Lett. 1 1999 225
64. H. Zipse J. Am. Chem. Soc. 119 1997 2889
65. S.N. Müller R. Batra M. Senn B. Giese M. Kisel O. Shadyro J. Am. Chem. Soc. 119 1997 2796
66. M. Newcomb J.H. Horner P.O. Whitted D. Crich X. Huang Q. Yao H. Zipse J. Am. Chem. Soc. 121 1999 10685
67. Wang, Y. and Zipse, H., Submitted for publication.
68. (a) V. Barone M. Cossi J. Tomasi J. Chem. Phys. 107 1997 3210
69. (b) V. Barone M. Cossi J. Phys. Chem. A 102 1998 1995
70. (c) C. Amovilli V. Barone R. Cammi E. Cances M. Cossi B. Mennucci C.S. Pomelli J. Tomasi Adv. Quant. Chem. 32 1998 227
71. D.M. Smith B.T. Golding L. Radom J. Am. Chem. Soc. 123 2001 1664
72. D.M. Smith B.T. Golding L. Radom J. Am. Chem. Soc. 121 1999 5700
73. P. George J.P. Glusker C.W. Bock J. Am. Chem. Soc. 119 1997 7065
74. P. George J.P. Glusker C.W. Bock J. Am. Chem. Soc. 117 1995 10131
75. B.T. Golding L. Radom J. Am. Chem. Soc. 98 1976 6331
76. D.M. Smith S.D. Wetmore L. Radom L.A. Ericksson Theoretical Biochemistry – Processes and Properties of Biological Systems 2001 Elsevier Amsterdam 183 214
77. (a) T. Toraya K. Yoshizawa M. Eda T. Yamabe J. Biochem. 126 1999 650
78. (b) M. Eda T. Kamachi K. Yoshizawa T. Toraya Bull. Chem. Soc. Jpn 75 2002 1469
79. S.D. Wetmore D.M. Smith J.T. Bennett L. Radom J. Am. Chem. Soc. 124 2002 14054
80. M. Semialjac H. Schwarz J. Am. Chem. Soc. 124 2002 8974
81. S.D. Wetmore D.M. Smith L. Radom J. Am. Chem. Soc. 123 2001 8678
82. S.D. Wetmore D.M. Smith L. Radom J. Am. Chem. Soc. 122 2000 10208
83. S. Hammerum Int. J. Mass Spectrom. 199 2000 71
84. B.F. Yates L. Radom Org. Mass Spectrom. 22 1987 430
85. S. Hammerum A.C. Petersen T.I. Sølling T. Vulpius H. Zappey J. Chem. Soc. Perkin Trans. 2 1997 391
86. T. Bjornholm S. Hammerum D. Kuck J. Am. Chem. Soc. 110 1988 3862
87. K.N. Houk Y. Li J.D. Evanseck Angew. Chem. Int. Ed. Engl. 31 1992 682
88. W.E. Doering Y. Wang J. Am. Chem. Soc. 121 1999 10112
89. (a) S. Shaik A. Shurki Angew. Chem. Int. Ed. Engl. 38 1999 586
90. N2 Transition State 1992 Wiley Interscience New York