Generation of alkene radical cations by heterolysis of β-Substituted radicals: Mechanism, stereochemistry, and applications in synthesis

Topics in Current Chemistry

Volumn 263, Issue , 2006, Pages 1-38

  Crich, David ^a   Brebion, Franck ^a   Suk, Dae Hwan ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

Alkene radical cations; Ion pairs; Kinetics; Stereochemical memory effects; Tandem reactions

Indexed keywords

EID: 33748877843     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_024     Document Type: Review

References (150)

1. Tanko JM, Phillips JP (1999) J Am Chem Soc 121:6078
2. Hintz S, Heidbreder A, Mattay J (1996) Top Curr Chem 177:77
3. Bauld NL, Bellville DJ, Harirchian B, Lorenz KT, Pabon RA, Reynolds DW, Wirth DD, Chiou H-S, Marsh BK (1987) Acc Chem Res 20:371
4. Schmittel M, Burghart A (1997) Angew Chem Int Ed 36:2550
5. Mangion D, Arnold DR (2002) Acc Chem Res 35:297
6. Dalko PI (1995) Tetrahedron 51:7579
7. Moeller KD (2000) Tetrahedron 56:9527
8. Little RD, Moeller KD (2002) Electrochem Soc Interface 11:36
9. Bauld NL, Roh Y (2002) Curr Org Chem 6:647
10. Nair V, Balagopal L, Rajan R, Mathew J (2004) Acc Chem Res 37:21
11. Ogibin YN, Nikishin GI (2001) Russ Chem Rev 70:543
12. Todres ZV (2003) Organic radical ions: chemistry and applications. Dekker, New York
13. Oelgemöller M, Bunte JO, Mattay J (2005) Mol Supramol Photochem 12:269
14. Wiest O, Oxgaard J, Saettel NJ, Adv Phys Org Chem 38:87
15. Moeller KD (1997) Top Curr Chem 185:49
16. Tabakovic I (1997) Top Curr Chem 185:87
17. Clark T (1996) Top Curr Chem 177:1
18. Sperry JB, Wright DL (2005) J Am Chem Soc 127:8034
19. Sperry JB, Constanzo JR, Jasinski J, Butcher RJ, Wright DL (2005) Tetrahedron Lett 46:2789
20. Sperry JB, Wright DL (2005) Tetrahedron Lett 46:411
21. Mihelcic J, Moeller KD (2004) J Am Chem Soc 126:9106
22. Huang Y-T, Moeller KD (2004) Org Lett 6:4199
23. Brandt JD, Moeller KD (2005) Tetrahedron Lett 7:3553
24. Fürmeier S, Metzger JO (2004) J Am Chem Soc 126:14485
25. Meyer S, Koch R, Metzger JO (2003) Angew Chem Int Ed 42:4700
26. Chiba K, Miura T, Kim S, Kitano Y, Tada M (2001) J Am Chem Soc 123:11314
27. Grützmacher H-F (2003) Curr Org Chem 7:1565
28. Bauld NL (1997) Radicals, radical ions, and triplets: the spin-bearing intermediates of organic chemistry. Wiley, New York
29. Rinderhagen H, Mattay J (2004) Chem Eur J 10:851
30. Bunte JO, Mattay J (2004) In: Horspool W, Lenci F (eds) CRC handbook of organic photochemistry and photobiology. CRC, Boca Raton, p 10/1
31. Bauld NL, Gao D (2001) In: Balzani V (ed) Electron transfer in chemistry and biochemistry, vol 2. Wiley, Weinheim, p 133
32. Gilbert BC, Larkin JP, Norman ROC (1972) J Chem Soc Perkin Trans 2:794
33. Behrens G, Koltzenburg G, Schulte-Frohlinde D (1982) Z Naturforsch 37c:1205
34. von Sonntag C (1987) The chemical basis of radiation biology. Taylor and Francis, London
35. von Sonntag C, Hagen U, Schon-Bopp A, Schulte-Frohlinde D (1981) In: Lett JT, Adler H (eds) Advances in radiation biology, vol 9. Academic, New York, p 109
36. von Sonntag C (1980) Adv Carbohydr Chem Biochem 37:7
37. Chatgilialoglu C, O'Neill P (2001) Exp Gerontol 36:1459
38. Glatthar R, Spichty M, Gugger A, Batra R, Damm W, Mohr M, Zipse H, Giese B (2000) Tetrahedron 56:4117
39. Pogozelski WK, Tullius TD (1998) Chem Rev 98:1089
40. Breen AP, Murphy JA (1995) Free Radie Biol Med 18:1033
41. Knorre DG, Fedorova OS, Frolova EI (1993) Russ Chem Rev 62:65
42. Pratviel G, Bernadou J, Meunier B (1995) Angew Chem Int Ed 34:746
43. Stubbe J, Kozarich JW, Wu W, Vanderwall DE (1996) Acc Chem Res 29:322
44. Dedon PC, Goldberg IH (1992) Chem Res Toxicol 5:311
45. Hecht SM (2000) J Nat Prod 63:158
46. Giese B (2000) Acc Chem Res 33:631
47. Giese B (2004) Top Curr Chem 236:27
48. Surzur J-M, Teissier P (1967) CR Acad Sci 264:1981
49. Crich D, Yao Q (1993) J Am Chem Soc 115:1165
50. Koch A, Lamberth C, Wetterich F, Giese B (1993) J Org Chem 58:1083
51. Beckwith ALJ, Crich D, Duggan PJ, Yao Q (1997) Chem Rev 97:3273
52. Crich D (2001) In: Renaud P, Sibi M (eds) Radicals in organic synthesis, vol 2. Wiley, Weinheim, p 188
53. Clark T, Nelsen SF (1988) J Am Chem Soc 110:868
54. Takahashi O, Kikuchi O (1994) J Mol Struct (Theochem) 313:207
55. Liu Y-J, Huang M-B (2001) J Mol Struct (Theochem) 536:133
56. Abrams MI, Valeev EF, Sherrill CD, Crawford TD (2002) J Phys Chem A 106:2671
57. Salhi-Benachenhou N, Engels B, Huang M-B, Lunell S (1998) Chem Phys 236:53
58. Kochi JK, Rathore R, Zhu J, Lindeman SV (2000) Angew Chem Int Ed 39:3671
59. Nelsen SF, Reinhardt LA, Tran HQ, Clark T, Chen G-F, Pappas RS, Williams F (2002) Chem Eur J 8:1074
60. Gerson F, Lopez J, Krebs A, Rüger W (1981) Angew Chem Int Ed 20:95
61. Behrens G, Bothe E, Koltzenberg G, Schulte-Frohlinde D (1980) J Chem Soc Perkin Trans 2:883
62. Behrens G, Koltzenburg G, Ritter A, Schulte-Frohlinde D (1978) Int J Radiat Biol 33:163
63. Koltzenburg G, Behrens G, Schulte-Frohlinde D (1982) J Am Chem Soc 104:7311
64. Müller SN, Batra R, Senn M, Giese B, Kisel M, Shadyro O (1997) J Am Chem Soc 119:2796
65. Giese B, Burger J, Kang TW, Kesselheim C, Wittmer T (1992) J Am Chem Soc 114:7322
66. Giese B, Beyrich-Graf X, Burger J, Kesselheim C, Senn M, Schafer T (1993) Angew Chem Int Ed 32:1742
67. Gugger A, Batra R, Rzadek P, Rist G, Giese B (1997) J Am Chem Soc 119:8740
68. Lancelot SF, Cozens FL, Schepp NP (2003) Org Biomol Chem 1:1972
69. Crich D, Suk D-H, Hao X (2002) Tetrahedron 58:5789
70. Crich D, Jiao X-Y (1996) J Am Chem Soc 118:6666
71. Beckwith ALJ, Duggan PJ (1996) J Am Chem Soc 118:12838
72. Beckwith ALJ, Thomas CB (1973) J Chem Soc Perkin Trans 2:861
73. Lacote E, Renaud P (1998) Angew Chem Int Ed 37:2259
74. Choi S-Y, Crich D, Horner JH, Huang X, Newcomb M, Whitted PO (1999) Tetrahedron 55:3317
75. Reichardt C (1994) Chem Rev 94:2319
76. Whitted PO, Horner JH, Newcomb M, Huang X, Crich D (1999) Org Lett 1:153
77. Newcomb M, Horner JH, Whitted PO, Crich D, Huang X, Yao Q, Zipse H (1999) J Am Chem Soc 121:10685
78. Bagnol L, Horner JH, Newcomb M (2003) Org Lett 5:5055
79. Bales BC, Horner JH, Huang X, Newcomb M, Crich D, Greenberg MM (2001) J Am Chem Soc 123:3623
80. Sprecher M (1994) Chemtracts 7:115
81. Winstein S, Clippinger E, Fainberg AH, Heck R, Robinson GC (1956) J Am Chem Soc 78:328
82. Richard JP, Amyes TI, Toteva MM, Tsuji Y (2004) Adv Phys Org Chem 39:1
83. Raber DJ, Harris JM, Schleyer PvR (1974) In: Szwarc M (ed) Ions and ion pairs in organic reactions, vol 2. Wiley, New York, p 247
84. Horner JH, Bagnol L, Newcomb M (2004) J Am Chem Soc 126:14979
85. Taxil E, Bagnol L, Horner JH, Newcomb M (2003) Org Lett 5:827
86. Horner JH, Taxil E, Newcomb M (2002) J Am Chem Soc 124:5402
87. Newcomb M, Miranda N, Huang X, Crich D (2000) J Am Chem Soc 122:6128
88. Arnold BR, Noukakis D, Farid S, Goodman JL, Gould IR (1995) J Am Chem Soc 117:4399
89. Newcomb M (1993) Tetrahedron 49:1151
90. Peukert S, Batra R, Giese B (1997) Tetrahedron Lett 38:3507
91. Schepp NP, Shukla D, Bauld NL, Johnston LJ (1997) J Am Chem Soc 119:10325
92. Lew CSQ, Brisson JR, Johnston LJ (1997) J Org Chem 62:4047
93. Behrens G, Bothe E, Koltzenburg G, Schulte-Frohlinde D (1981) J Chem Soc Perkin Trans 2:143
94. Johnston LJ, Schepp NP (1993) J Am Chem Soc 115:6564
95. Johnston LJ, Schepp NP (1996) Adv Electron Transfer Chem 5:41
96. Johnston LJ, Schepp NP (1995) Pure Appl Chem 67:71
97. Saebo S, Beckwith ALJ, Radom L (1984) J Am Chem Soc 106:5119
98. Zipse H (2003) Adv Phys Org Chem 38:111
99. Barclay LRC, Griller D, Ingold KU (1982) J Am Chem Soc 104:4399
100. Wang Y, Grimme S, Zipse H (2004) J Phys Chem A 108:2324
101. Zipse H, Bootz M (2001) J Chem Soc Perkin Trans 2:1566
102. Zipse H (1994) Angew Chem Int Ed 33:1985
103. Zipse H (1999) Acc Chem Res 32:571
104. Peukert S, Giese B (1996) Tetrahedron Lett 37:4365
105. Clive DLJ, Chittattu GJ, Farina V, Kiel WA, Menchen SM, Russell CG, Singh A, Wong CK, Curtis N (1980) J Am Chem Soc 102:4438
106. Beckwith ALJ, Pigou PE (1986) Aus J Chem 39:77
107. Filzen GF (1996) PhD thesis, University of Illinois at Chicago
108. Crich D (1987) Aldrichim Acta 20:35
109. Crich D, Quintero L (1989) Chem Rev 89:1413
110. Motherwell WB, Imboden C (2001) In: Renaud P, Sibi MP (eds) Radicals in organic synthesis, vol 1. Wiley, Weinheim, p 109
111. Crich D, Huang X, Newcomb M (2000) J Org Chem 65:523
112. Crich D, Huang W (2001) J Am Chem Soc 123:9239
113. Ono N, Miyake H, Kamimura A, Hamamoto I, Tamura R, Kaji A (1985) Tetrahedron 41:4013
114. Ono N (2001) The nitro group in organic synthesis. Wiley, New York
115. Giese B, Groninger KS (1990) Org Synth 69:66
116. Giese B, Gilges S, Groninger KS, Lamberth C, Witzel T (1988) Liebigs Ann Chem 615
117. Quiclet-Sire B, Zard SZ (1996) J Am Chem Soc 118:9190
118. Korth H-G, Sustmann R, Groninger KS, Leisung M, Giese B (1988) J Org Chem 53:4364
119. Crich D, Yao Q, Filzen GF (1995) J Am Chem Soc 117:11455
120. Kocovsky P, Stary I, Turecek F (1986) Tetrahedron Lett 27:1513
121. Beckwith ALJ, Duggan PJ (1992) J Chem Soc Perkin Trans 2:1777
122. Beckwith ALJ, Duggan PJ (1998) Tetrahedron 54:4623
123. Beckwith ALJ, Duggan PJ (1998) Tetrahedron 54:6919
124. Crich D, Beckwith ALJ, Filzen GF, Longmore RW (1996) J Am Chem Soc 118:7422
125. Crich D, Huang X, Beckwith ALJ (1999) J Org Chem 64:1762
126. Crich D, Sartillo-Piscil F, Quintero-Cortes L, Wink DJ (2002) J Org Chem 67:3360
127. Crich D, Suk D-H (2004) Can J Chem 82:75
128. Crich D, Suk D-H, Sun S (2003) Tetrahedron Asymmetry 14:2861
129. Clive DLJ (1975) J Chem Soc Chem Commun: 353
130. Beckwith ALJ (1981) Tetrahedron 37:3073
131. Suk D-H (2004) PhD thesis, University of Illinois at Chicago
132. Koch A, Giese B (1993) Helv Chim Acta 76:1687
133. Walling C, Cioffari A (1972) J Am Chem Soc 94:6064
134. Crich D, Gastaldi S (1998) Tetrahedron Lett 39:9377
135. Crich D, Huang X, Newcomb M (1999) Org Lett 1:225
136. Sartillo-Piscil F, Vargas M, Anaya de Parrodi C, Quintero I. (2003) Tetrahedron Lett 44:3919
137. Kim S, Lee TA, Song Y (1998) Synlett 501
138. Kabasakalian P, Townley ER, Yudis MD (1962) J Am Chem Soc 84:2716
139. Crich D, Ranganathan K, Neelamkavil S, Huang X (2003) J Am Chem Soc 125:7942
140. Crich D, Neelamkavil S (2002) Org Lett 4:2573
141. Crich D, Shirai M, Rumthao S (2003) Org Lett 5:3767
142. Crich D, Shirai M, Brebion F, Rumthao S (2006) Tetrahedron (in press)
143. Crich D, Ranganathan K, Huang X (2001) Org Lett 3:1917
144. Crich D, Ranganathan K (2002) J Am Chem Soc 124:12422
145. Crich D, Ranganathan K (2005) J Am Chem Soc 127:9924
146. Beckwith ALJ, Schiesser CH (1985) Tetrahedron 41:3925
147. Spellmeyer DC, Houk KN (1987) J Org Chem 52:959
148. Curran DP, Porter NA, Giese B (1996) Stereochemistry of radical reactions. Wiley, Weinheim
149. Liu B, Duan S, Sutterer AC, Moeller KD (2002) J Am Chem Soc 124:10101
150. Bunte JO, Heilmann EK, Hein B, Mattay J (2004) Eur J Org Chem 3535