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Oxidations and Rearrangements

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 224))

Abstract

Oxidations and rearrangements using hypervalent iodine compounds are summarized in this review with emphasis on synthetic applications of these procedures. New reagents and polymer-supported versions are highlighted which facilitate the use of hypervalent iodine compounds in these reactions. Beside the more traditional oxidation of sulfides to sulfoxides and of alcohols to the corresponding ketones, the functionalization of activated carbon-hydrogen bonds in the oxidation in carbonyl compounds and the functionalization of only slightly activated carbon-hydrogen bonds in benzylic positions are discussed. New rearrangements using hypervalent iodine compounds are finally mentioned.

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References

  1. Varvoglis A (1984) Synthesis 709

    Google Scholar 

  2. Moriarty RM, Prakash O (1986) Acc Chem Res 19:244

    Article  CAS  Google Scholar 

  3. Varvoglis A (1992) The Organic Chemistry of Polycoordinated Iodine, 1st edn. VCH, Weinheim

    Google Scholar 

  4. Varvoglis A (1997) Hypervalent Iodine in Organic Synthesis, 1st edn. Academic Press, London

    Google Scholar 

  5. Moriarty RM, Prakash O (1998) Adv Heterocyclic Chem 69:1

    Article  CAS  Google Scholar 

  6. Moriarty RM, Prakash O (1999) Org React 54:273

    CAS  Google Scholar 

  7. Wirth T, Hirt UH (1999) Synthesis 1271

    Google Scholar 

  8. Togo H, Katohki M (2001) Synlett 565

    Google Scholar 

  9. Willgerodt C (1886) J Prakt Chem 33:154

    Article  Google Scholar 

  10. Pohnert G (2000) J Prakt Chem 342:731

    Article  CAS  Google Scholar 

  11. Neilands O, Karele B (1970) Zh Org Khim 6:885

    CAS  Google Scholar 

  12. Koser GF, Wettach RH, Troup JM, Frenz BA (1976) J Org Chem 41:3609

    Article  CAS  Google Scholar 

  13. Koser GF, Wettach RH (1977) J Org Chem 42:1476

    Article  CAS  Google Scholar 

  14. Hartmann C, Meyer V (1893) Chem Ber 26:1727

    Article  Google Scholar 

  15. Dess DB, Martin JC (1991) J Am Chem Soc 113:7277

    Article  CAS  Google Scholar 

  16. Wirth T (2001) Angew Chem Int Ed 40:2812

    Article  CAS  Google Scholar 

  17. Dess DB, Martin JC (1983) J Org Chem 43:4155

    Article  Google Scholar 

  18. Thottumkara AP, Vinod TK (2002) Tetrahedron Lett 43:569

    Article  CAS  Google Scholar 

  19. Katritzky AR, Duell BL, Durst HP, Knier BL (1988) J Org Chem 53:3972

    Article  CAS  Google Scholar 

  20. Nicolaou KC, Montagnon T, Baran PS (2002) Angew Chem Int Ed 41:993

    Article  CAS  Google Scholar 

  21. Macikenas D, Meprathu BV, Protasiewicz JD (1998) Tetrahedron Lett 39:191

    Article  CAS  Google Scholar 

  22. Takada H, Nishibayashi Y, Ohe K, Uemura S (1996) Chem Commun 931

    Google Scholar 

  23. O’Connor KJ, Wey SJ, Burrows CJ (1992) Tetrahedron Lett 33:1001

    Article  CAS  Google Scholar 

  24. Noda K, Hosoya N, Irie R, Ito Y, Katsuki T (1993) Synlett 469

    Google Scholar 

  25. Nishikori H, Katsuki T (1996) Tetrahedron Lett 37:9245

    Article  CAS  Google Scholar 

  26. Stickley SH, Martin JC (1995) Tetrahedron Lett 36:9117

    Article  CAS  Google Scholar 

  27. Moss RA, Zhang H (1994) J Am Chem Soc 116:4471

    Article  CAS  Google Scholar 

  28. Zhandkin VV, Smart JT, Zhao P, Kiprof P (2000) Tetrahedron Lett 41:5299

    Article  Google Scholar 

  29. Togo H, Nabana T, Yamaguchi K (2000) J Org Chem 65:8391

    Article  CAS  Google Scholar 

  30. Togo H, Naka T, Onosawa T (2001) Jap Patent 2000-115898

    Google Scholar 

  31. Zhdankin VV, Kuehl CJ, Simonsen AJ (1996) J Org Chem 61:8272

    Article  CAS  Google Scholar 

  32. Aki S, Okuno T, Takada T, Tohma H, Kita Y (1998) Heterocycles 42:47

    Google Scholar 

  33. Zhdankin VV, Arbit RM, McSherry M, Mismash B, Young VG (1997) J Am Chem Soc 119:7408

    Article  CAS  Google Scholar 

  34. Zhdankin VV, Arbit RM, Lynch BJ, Kiprof P (1998) J Org Chem 63:6590

    Article  CAS  Google Scholar 

  35. Dörwald FZ (2000) Organic Synthesis on Solid Phase, 1st edn. Wiley-VCH, Weinheim

    Google Scholar 

  36. Yamada Y, Okawara M (1972) Makromol Chem 152:153

    Article  CAS  Google Scholar 

  37. Hallersleben ML (1972) Angew Makromol Chem 27:223

    Article  Google Scholar 

  38. Zupan M (1977) Collect Czech Chem Commun 42:266

    CAS  Google Scholar 

  39. Tohma H, Morioka H, Takizawa S, Arisawa M, Kita Y (2001) Tetrahedron 57:345

    Article  CAS  Google Scholar 

  40. Togo H, Nogami G, Yokoyama M (1998) Synlett 534

    Google Scholar 

  41. Ley SV, Thomas AW, Finch H (1999) J Chem Soc Perkin Trans 1 669

    Article  Google Scholar 

  42. Wang GP, Chen ZC (1999) Synth Commun 29:2859

    Article  CAS  Google Scholar 

  43. Ficht S, Mülbaier M, Giannis A (2001) Tetrahedron 57:4863

    Article  CAS  Google Scholar 

  44. Mülbaier M, Giannis A (2001) Angew Chem Int Ed 40:4393

    Article  Google Scholar 

  45. Sorg G, Mengel A, Jung G, Rademann J (2001) Angew Chem Int Ed 40:4395

    Article  CAS  Google Scholar 

  46. Roh KR, Kim KS, Kim YH (1991) Tetrahedron Lett 32:793

    Article  CAS  Google Scholar 

  47. Yang R, Dai L (1994) Synth Commun 24:2229

    Article  CAS  Google Scholar 

  48. Xia M, Chen ZC (1997) Synth Commun 27:1315

    Article  CAS  Google Scholar 

  49. Tohma H, Takizawa S, Watanabe H, Kita Y (1998) Tetrahedron Lett 39:4547

    Article  CAS  Google Scholar 

  50. Ochiai M, Nakanishi A, Ito T (1997) J Org Chem 62:4253

    Article  CAS  Google Scholar 

  51. Ou W, Chen ZC (1999) Synth Commun 29:4443

    Article  CAS  Google Scholar 

  52. Noda K, Hosoya N, Irie R, Yamashita Y, Katsuki T (1994) Tetrahedron 50:9609

    Article  CAS  Google Scholar 

  53. Imamoto T, Koto H (1986) Chem Lett 967

    Google Scholar 

  54. Hatzigrigoriou E, Varvoglis A, Bakola-Christianopoulou M (1990) J Org Chem 55:315

    Article  CAS  Google Scholar 

  55. Ray DG, Koser GF (1992) J Org Chem 57:1607

    Article  CAS  Google Scholar 

  56. Wirth T, Hirt UH (1997) Tetrahedron: Asymmetry 8:23

    Article  CAS  Google Scholar 

  57. Tohma H, Takizawa S, Watanabe H, Fukuoka Y, Maegawa T, Kita Y (1999) J Org Chem 64:3519

    Article  CAS  Google Scholar 

  58. Tohma H, Takizawa S, Morioka H, Maegawa T, Kita Y (2000) Chem Pharm Bull 48:445

    CAS  Google Scholar 

  59. Xia M, Chen ZC (1997) Synth Commun 27:1321

    Article  CAS  Google Scholar 

  60. Xia M, Chen ZC (1997) Synth Commun 27:1301

    Article  CAS  Google Scholar 

  61. Xia M, Chen ZC (1997) Synth Commun 27:1309

    Article  CAS  Google Scholar 

  62. Chen D, Chen Z (1994) Tetrahedron Lett 35:7627

    Google Scholar 

  63. Xia M, Chen Z (1995) Synth Commun 25:1605

    Article  Google Scholar 

  64. Huwe CM, Künzer H (1999) Tetrahedron Lett 40:683

    Article  CAS  Google Scholar 

  65. Ireland RE, Liu L (1993) J Org Chem 58:2899

    Article  CAS  Google Scholar 

  66. Meyer SDM, Schreiber SL (1994) J Org Chem 59:7549

    Article  CAS  Google Scholar 

  67. Greenbaum FR (1936) Am J Pharm 108:17

    CAS  Google Scholar 

  68. Frigerio M, Santagostino M (1994) Tetrahedron Lett 35:8019

    CAS  Google Scholar 

  69. Frigerio M, Santagostino M, Sputore S, Palmisano G (1995) J Org Chem 60:7272

    Article  CAS  Google Scholar 

  70. Maiti A, Yadav JS (2001) Synth Commun 31:1499

    Article  CAS  Google Scholar 

  71. De Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G (1997) J Org Chem 62:6974

    Article  Google Scholar 

  72. Tasler S, Endress H, Bringmann G (2001) Synthesis 1993

    Google Scholar 

  73. Tohma H, Takizawa S, Maegawa T, Kita Y (2000) Angew Chem Int Ed 39:1306

    Article  CAS  Google Scholar 

  74. Kirschning A, Hary U, Plumeier C, Ries M, Rose L (1999) J Chem Soc Perkin Trans 1 519

    Article  Google Scholar 

  75. Kirschning A (1995) Liebigs Ann 2053

    Google Scholar 

  76. Kirschning A (1995) J Org Chem 60:1228

    Article  CAS  Google Scholar 

  77. Kirschning A (1998) Eur J Org Chem 2267

    Google Scholar 

  78. Drutu I, Njardarson JT, Wood JL (2002) Org Lett 4:493

    Article  CAS  Google Scholar 

  79. Karam O, Martin A, Jouannetaud MP, Jacquessy JC (1999) Tetrahedron Lett 40:4183

    Article  CAS  Google Scholar 

  80. Mitchell AS, Russell RA (1997) Tetrahedron 53:4387

    Article  CAS  Google Scholar 

  81. Quideau S, Pouységu L, Avellan AV, Whelligan DK, Looney MA (2001) Tetrahedron Lett 42:7393

    Article  CAS  Google Scholar 

  82. Carlini R, Fang CL, Herrington D, Higgs K, Russell R, Taylor N (1997) Aust J Chem 50:271

    Article  CAS  Google Scholar 

  83. Kürti L, Szilágyi L, Antus S, Nógrádi M (1999) Eur J Org Chem 2579

    Google Scholar 

  84. Mal D, Roy HN, Hazra NK, Adhikari S (1997) Tetrahedron 53:2177

    Article  CAS  Google Scholar 

  85. Kato N, Sugaya T, Mimura T, Ikuta M, Kato S, Kuge Y, Tomioka S, Kasai M (1997) Synthesis 625

    Google Scholar 

  86. Wells G, Bradshaw TD, Diana P, Seaton A, Shi DF, Westwell AD, Stevens MFG (2000) Bioorg Med Chem Lett 10:513

    Article  CAS  Google Scholar 

  87. Wells G, Seaton A, Stevens MFG (2000) J Med Chem 43:1550

    Article  CAS  Google Scholar 

  88. Saitz CB, Valderrama JA, Tapia R, Farina F, Paredes MC (1992) Synth Commun 22:955

    Article  Google Scholar 

  89. Pelter P, Elgendy SMA (1993) J Chem Soc Perkin Trans 1 1891

    Article  Google Scholar 

  90. Farina F, del Carmen Paredes M, Sato J (1995) J An Quim 91:50

    CAS  Google Scholar 

  91. Kato N, Sugaya T, Mimura T, Ikuta M, Kato S, Kuge Y, Tomioka S, Kasai M (1997) Synthesis 625

    Google Scholar 

  92. Kinugawa M, Masuda Y, Arai H, Nishikawa H, Ogasa T, Tomioka S, Kasai M (1996) Synthesis 633

    Google Scholar 

  93. Thoma H, Morioka H, Harayama Y, Hashizume, M, Kita Y (2001) Tetrahedron Lett 42:6899

    Article  Google Scholar 

  94. Magdyiak D, Rodriguez AA, Van De Water RW, Pettus TRR (2002) Org Lett 4:285

    Article  CAS  Google Scholar 

  95. Nicolaou KC, Baran PS, Zhong YL, Sugita K (2002) J Am Chem Soc 124:2212

    Article  CAS  Google Scholar 

  96. Nicolaou KC, Sugita K, Baran PS, Zhong YL (2002) J Am Chem Soc 124:2221

    Article  CAS  Google Scholar 

  97. Nicolaou KC, Sugita K, Baran PS, Zhong YL (2001) Angew Chem Int Ed 40:207

    Article  CAS  Google Scholar 

  98. Singh SP, Kumar D, Prakash O, Kapoor RP (1997) Synth Commun 27:2683

    Article  CAS  Google Scholar 

  99. Aly MF, Younes MI, Metwally SAM (1994) Tetrahedron 50:3159

    Article  CAS  Google Scholar 

  100. Gupta P, Bhaduri A (1998) Synth Commun 28:3151

    Article  CAS  Google Scholar 

  101. Varma RS, Kumar D (1998) Tetrahedron Lett 39:9113

    Article  CAS  Google Scholar 

  102. Prakash O, Tanwar MP (1995) J Chem Res Synop 213

    Google Scholar 

  103. Prakash O, Tanwar MP (1995) Bull Chem Soc Jpn 68:1168

    Article  CAS  Google Scholar 

  104. Cheng DP, Chen ZC (2002) Synth Commun 32:793

    Article  CAS  Google Scholar 

  105. Moriarty RM, Hu H, Gupta SC (1981) Tetrahedron Lett 22:1283

    Article  CAS  Google Scholar 

  106. Moriarty RM, Hou KC (1984) Tetrahedron Lett 25:691

    Article  CAS  Google Scholar 

  107. Yasuda S, Yamada T, Hanaoka M (1986) Tetrahedron Lett 27:2023

    Article  CAS  Google Scholar 

  108. Moriarty RM, John LS, Du PC (1981) J Chem Soc Chem Commun 641

    Google Scholar 

  109. Daum SJ (1984) Tetrahedron Lett 25:4725

    Article  CAS  Google Scholar 

  110. Moriarty RM, Prakash O, Duncan MP (1985) Synthesis 943

    Google Scholar 

  111. Moriarty RM, Duncan MP, Prakash O (1987) J Chem Soc Perkin Trans 1 1781

    Article  Google Scholar 

  112. Moriarty RM, Rani N, Condeiu C, Duncan MP, Prakash O (1997) Synth Commun 27:3273

    Article  CAS  Google Scholar 

  113. Merkushev EB, Novikov AN, Makarchenko SS, Moskal’chuk AS, Glushkova VV, Kogai TI, Polyakova LG (1975) J Org Chem USSR Engl Transl 11:1246

    Google Scholar 

  114. Ochiai M, Takaoka Y, Masaki Y, Nagao Y, Shiro M (1990) J Am Chem Soc 112:5677

    Article  CAS  Google Scholar 

  115. Rabah GA, Koser GF (1996) Tetrahedron Lett 37:6453

    Article  CAS  Google Scholar 

  116. Ray DG, Koser GF (1990) J Am Chem Soc 112:5672

    Article  CAS  Google Scholar 

  117. Kitamura T, Lee CH, Taniguchi Y, Fujiwara Y (1997) J Am Chem Soc 119:619

    Article  CAS  Google Scholar 

  118. Hirt UH, Spingler B, Wirth T (1998) J Org Chem 63:7674

    Article  CAS  Google Scholar 

  119. Hirt UH, Schuster MFH, French AN, Wiest OG, Wirth T (2001) Eur J Org Chem 1569

    Google Scholar 

  120. Singh SP, Naithani R, Aggarwal R, Prakash O (1998) Synth Commun 28:2371

    Article  CAS  Google Scholar 

  121. Singh SP, Naithani R, Aggarwal R, Prakash O (2001) Synth Commun 31:3747

    Article  CAS  Google Scholar 

  122. Zhang PF, Chen ZC (2001) Synth Commun 31:415

    Article  CAS  Google Scholar 

  123. Zhang PF, Chen ZC (2001) Synthesis 2075

    Google Scholar 

  124. Nicolaou KC, Montagnon T, Ulven T, Baran PS, Zhong YL, Sarabia F (2002) J Am Chem Soc 124: in press

    Google Scholar 

  125. Nicolaou KC, Montagnon T, Baran PS, Zhong YL (2002) J Am Chem Soc 124:2245

    Article  CAS  Google Scholar 

  126. Nicolaou KC, Zhong YL, Baran PS (2000) J Am Chem Soc 122:7596

    Article  CAS  Google Scholar 

  127. Nicolaou KC, Montagnon T, Baran PS (2002) Angew Chem Int Ed 41:993

    Article  CAS  Google Scholar 

  128. Nicolaou KC, Gray DLF, Montagnon T, Harrison ST (2002) Angew Chem Int Ed 41:996

    Article  CAS  Google Scholar 

  129. Nicolaou KC, Montagnon T, Baran PS (2002) Angew Chem Int Ed 41:1386

    Article  CAS  Google Scholar 

  130. Dolenc D, Plesnicar B (1997) J Am Chem Soc 119:2628

    Article  CAS  Google Scholar 

  131. Ochiai M, Kajishima D, Sueda T (1997) Heterocycles 46:71

    Article  CAS  Google Scholar 

  132. Ochiai M, Ito T, Takahashi H, Nakanishi A, Toyonari M, Sueda T, Goto S, Shiro M (1996) J Am Chem Soc 118:7716

    Article  CAS  Google Scholar 

  133. Carlsen PHJ, Katsuki T, Martin VS, Sharpless KB (1981) J Org Chem 46:3936

    Article  CAS  Google Scholar 

  134. Bal BS, Kochhar KS, Pinnick HW (1981) J Org Chem 46:1492

    Article  CAS  Google Scholar 

  135. Nicolaou KC, Baran PS, Zhong YL (2001) J Am Chem Soc 123:3183

    Article  CAS  Google Scholar 

  136. Moriarty RM, Chany CJ, Vaid RK, Prakash O, Tuladhar SM (1993) J Org Chem 58:2478

    Article  CAS  Google Scholar 

  137. Larbin IM, Koser GF (1987) J Org Chem 52:476

    Article  Google Scholar 

  138. Almond MR, Loudon GM, Stimmel JB, Thompson AE (1988) Org Synth 67:132

    Google Scholar 

  139. Della EW, Kasum B, Kirkbride KP (1987) J Am Chem Soc 109:2746

    Article  CAS  Google Scholar 

  140. Prakash O, Batra H, Kaur H, Sharma PK, Sharma V, Singh SP, Moriarty RM (2001) Synthesis 541

    Google Scholar 

  141. Ramsden CA, Rose HL (1997) J Chem Soc Perkin Trans 1 2319

    Article  Google Scholar 

  142. Tiecco M, Testaferri L, Tingoli M, Bartoli D (1990) Tetrahedron 46:7139

    Article  CAS  Google Scholar 

  143. Boye A, Wirth T (2001) unpublished results

    Google Scholar 

  144. Miki Y, Fujita R, Matsushita K (1998) J Chem Soc Perkin Trans 1 2533

    Article  Google Scholar 

  145. Gately DA, Luther TA, Norton JR, Miller MM, Anderson OP (1992) J Org Chem 57:6496

    Article  CAS  Google Scholar 

  146. Ochiai M, Ito T, Takaoka Y, Masaki Y (1991) J Am Chem Soc 113:1319

    Article  CAS  Google Scholar 

  147. Ochiai M, Ito T, Masaki Y (1992) J Chem Soc Chem Commun 15

    Google Scholar 

  148. Kida M, Sueda T, Goto S, Okuyama T, Ochiai M (1996) Chem Commun 1933

    Google Scholar 

  149. Ochiai M, Ito T (1995) J Org Chem 60:2274

    Article  CAS  Google Scholar 

  150. Ochiai M, Kida M, Okuyama T (1998) Tetrahedron Lett 39:6207

    Article  CAS  Google Scholar 

  151. Blechert S (1989) Synthesis 71

    Google Scholar 

  152. Wipf P, Venkatraman S (1996) J Org Chem 61:8004

    Article  CAS  Google Scholar 

  153. De Mico A, Margarita R, Piancatelli G (1995) Gazz Chim Ital 125:325

    Google Scholar 

  154. Prakash O, Sharma V, Tanwar MP (1999) Can J Chem 77:1191

    Article  CAS  Google Scholar 

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Wirth, T. (2003). Oxidations and Rearrangements. In: Wirth, T. (eds) Hypervalent Iodine Chemistry. Topics in Current Chemistry, vol 224. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-46114-0_7

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