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High dilution reactions — New synthetic applications

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Macrocycles

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 161))

Abstract

The chemistry of medio- and macrocycles experienced an impetuous development during the past years, especially through the increasing significance of supramolecular chemistry [1] which was valued in 1987 by awarding the Nobel Prize to Pedersen, Cram, and Lehn [2].

The following contribution is intended to explain recent syntheses of macrocycles using the dilution principle after giving a short introduction into the basics of dilution principle reactions [3].

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7 References

  1. Vögtle F (1989) Supramolekulare Chemie — Eine Einführung, Teubner, Stuttgart

    Google Scholar 

  2. Weber E, Vögtle F (1987) Nachr Chem Tech Lab 35: 1149

    Google Scholar 

  3. Rossa L, Vögtle F (1983) Top Curr Chem 113: 1

    Google Scholar 

  4. Tabushi I, Yamamura K (1983) Top Curr Chem 113: 145

    Google Scholar 

  5. Kiggen W, Vögtle F (1987) In: Izatt RM, Christensen JJ (eds), Synthesis of macrocycles: The design of selective complexing agents, Wiley, New York, p 309

    Google Scholar 

  6. Vögtle F (1972) Chem-Ztg 96: 396

    Google Scholar 

  7. Karbach S, Löhr W, Vögtle F (1981) J Chem Res (S) 314; (1981) J Chem Res (M) 3579

    Google Scholar 

  8. Christen HR, Vögtle F (1990), Organische Chemie — Von den Grundlagen zur Forschung, Bd II, Salle-Sauerländer, Frankfurt/Aarau

    Google Scholar 

  9. Ruggli P (1912) Liebigs Ann Chem 392: 92

    Google Scholar 

  10. Ziegler K (1955) In: Houben-Weyl 4/2, p 729

    Google Scholar 

  11. Diederich F, Staab HA (1978) Angew Chem 90: 383; (1978) Angew Chem, Int Ed Engl 17: 372

    Google Scholar 

  12. Meurer K, Vögtle F, Mannschreck A, Stühler G, Puff H, Roloff A (1984) J Org Chem 49: 3484

    Article  Google Scholar 

  13. Vögtle F, Przybilla KJ, Mannschreck A, Pustet N, Büllesbach P, Reuter H, Puff H (1988) Chem Ber 121: 823

    Google Scholar 

  14. Vögtle F, Struck J, Puff H, Woller P, Reuter H (1986) J Chem Soc, Chem Commun 1248

    Google Scholar 

  15. Vögtle F, Mittelbach K, Struck J, Nieger M (1989) ibid 65

    Google Scholar 

  16. Przybilla KJ, Vögtle F (1988) Chem Ber 122: 347

    Google Scholar 

  17. Klieser B, Rossa L, Vögtle F (1984) Kontakte (Darmstadt) 1: 3

    Google Scholar 

  18. Koepp E, Vögtle F (1987) Synthesis 177

    Google Scholar 

  19. Vögtle F, Klieser B (1982) Synthesis 294

    Google Scholar 

  20. Navarro P, Rodriguez-Franco MI, Samat A (1987) Synth Commun 17: 105

    Google Scholar 

  21. Kruizinga WH, Kellogg RM (1981) J Am Chem Soc 103: 5183

    Article  Google Scholar 

  22. Review: Laider DA, Stoddart JF (1980) In: Patai S (ed), The chemistry of functional groups, Suppl E, part 1, Wiley, New York, p 1–15

    Google Scholar 

  23. Bowsher BR, Rest AJ (1981) J Chem Soc, Dalton Trans 1157

    Google Scholar 

  24. Kulstad S, Malmsten LA (1980) Tetrahedron 36: 521

    Article  Google Scholar 

  25. Shanzer A, Mayer-Shochet N (1980) J Chem Soc, Chem Commun 176

    Google Scholar 

  26. Poon CK, Che CM (1979) J Chem Soc, Chem Commun 861

    Google Scholar 

  27. Dietrich-Buchecker CO, Guilhelm J, Khemiss AK, Kintzinger JP, Pascard C, Sauvage JP (1987) Angew Chem 99: 711; (1987) Angew Chem, Int Ed Engl 26: 661

    Google Scholar 

  28. Dietrich-Buchecker CO, Khemiss A, Sauvage JP (1986) J Chem Soc, Chem Commun 1376

    Google Scholar 

  29. Shanzer A, Libman J (1983) J Chem Soc, Chem Commun 846

    Google Scholar 

  30. Saigo K, Lin RJ, Kubo M, Youda A, Hasegawa M (1986) J Am Chem Soc 108: 1996

    Article  Google Scholar 

  31. Healy MDS, Rest AJ (1978) Adv Inorg Chem Radiochem 21: 1

    Google Scholar 

  32. Galli C, Mandolini L (1982) J Chem Soc, Chem Commun 251

    Google Scholar 

  33. Hammerschmidt E, Schlüter H, Vögtle F (1980) J Chem Res (S) 86; ibid (M) 1083

    Google Scholar 

  34. Mattice WL, Newkome GR (1982) J Am Chem Soc 104: 5942

    Article  Google Scholar 

  35. Fastrez J (1987) Tetrahedron Lett 28: 419

    Article  Google Scholar 

  36. Chojnowski J, Rubinsztajn S, Wilczek L (1983) J Chem Soc, Chem Commun 69

    Google Scholar 

  37. Hammond PJ, Beer PD, Hall CD (1983) J Chem Soc, Chem Commun 1161

    Google Scholar 

  38. Review: Illuminati G, Mandolini L (1981) Acc Chem Res 14: 95

    Article  Google Scholar 

  39. Illuminati G, Mandolini L, Masci B (1981) J Am Chem Soc 103: 4142

    Article  Google Scholar 

  40. Winnik MA (1981) Chem Rev 81: 491

    Article  Google Scholar 

  41. Rodgers SJ, Ng CY, Raymond KN (1985) J Am Chem Soc 107: 4094

    Article  Google Scholar 

  42. Vögtle F, Nieger M, Przybilla KJ, Franken S (1988) Angew Chem 100: 987; (1988) Angew Chem, Int Ed Engl 27: 976

    Google Scholar 

  43. Sato T, Torizuka K, Komaki R, Atobe H (1980) J Chem Soc, Perkin II 561

    Google Scholar 

  44. Rheingold ID, Schmidt W, Boekelheide V (1979) J Am Chem Soc 101: 2121

    Article  Google Scholar 

  45. Kißener W, Vögtle F (1985) Angew Chem 97: 782; (1985) Angew Chem, Int Ed Engl 24: 794

    Google Scholar 

  46. Mitchell RH, Chaudhary M, Kamada T, Slowey PD, Williams RV (1986) Tetrahedron 42: 1741

    Article  Google Scholar 

  47. Schriver JW, Thomas TA (1987) J Am Chem Soc 109: 4121

    Article  Google Scholar 

  48. Struck J (1986) PD thesis, University of Bonn

    Google Scholar 

  49. Bodwell G, Ernst L, Hopf H (1989) Chem Ber 122: 1013

    Google Scholar 

  50. Bolm C, Sharpless KB (1988) Tetrahedron Lett 29: 5101

    Article  Google Scholar 

  51. Bodwell G, Ernst L, Haenel MW, Hopf H (1989) Angew Chem 101: 509; (1989) Angew Chem, Int Ed Engl 28: 455

    Google Scholar 

  52. Sendhoff N, Weißbarth KH, Vögtle F (1987) Angew Chem 99: 794; (1987) Angew Chem, Int Ed Engl. 26: 777

    Google Scholar 

  53. Sendhoff N, Kißener W, Vögtle F, Franken S, Puff H (1988) Chem Ber 121: 2179

    Google Scholar 

  54. Tashiro M, Yamato T, Kobayashi K, Arimura T (1987) J Org Chem 52: 3196

    Article  Google Scholar 

  55. Hisatome M, Yoshihashi M, Yamakawa K, Iitaka Y (1987) Bull Chem Soc Jpn 60: 2953

    Google Scholar 

  56. Pascal Jr RA, Winans CG, Van Engen D (1989) J Am Chem Soc 111: 3007

    Article  Google Scholar 

  57. Cordes AW, Lin ST, Lin LH (1990) Acta Crystallogr C46: 170

    Google Scholar 

  58. Kawashima T, Kurioka S, Tohda Y, Ariga M, Mori Y (1985) Chem Lett 1289

    Google Scholar 

  59. Funhoff DJH, Staab HA (1986) Angew Chem 98: 757; (1986) Angew Chem, Int Ed Engl 25: 742

    Google Scholar 

  60. Rau H, Lüddecke E (1982) J Am Chem Soc 104: 1616

    Article  Google Scholar 

  61. Butcher Jr JA, Dutta AK (1986) Tetrahedron Lett 27: 3341

    Article  Google Scholar 

  62. Vögtle F, Saitmacher K, Peyerimhoff S, Hippe D, Puff H, Büllesbach P (1987) Angew Chem 99: 459; (1987) Angew Chem, Int Ed Engl 26: 470

    Google Scholar 

  63. Billen S, Vögtle F (1989) Chem Ber 122: 1113

    Google Scholar 

  64. Dittrich U, Grützmacher HF (1985) Chem Ber 118: 4404

    Google Scholar 

  65. Meurer K, Luppertz F, Vögtle F (1985) Chem Ber 118: 4433

    Google Scholar 

  66. Ostrowicki A, Vögtle F (1988) Synthesis 1003

    Google Scholar 

  67. Sergeev VA, Ovchinnikov YE, Nedel'Kin VI, Astankov AV, Andrianova OB, Shklover VE, Zamaev IA, Struchkov YT (1988) Izv Akad Nauk SSSR, Ser Khim 1625

    Google Scholar 

  68. Mashraqui SH, Keehn PM (1983) J Org Chem 48: 1341

    Article  Google Scholar 

  69. Otsubo T, Kohda T, Misumi S (1980) Bull Chem Soc Jpn 53: 512

    Google Scholar 

  70. Machida H, Tatemitsu H, Otsubo T, Sakata Y, Misumi S (1980) Bull Chem Soc Jpn 53: 2943

    Google Scholar 

  71. Nakazaki M, Yamamoto K, Toya T (1981) J Org Chem 46: 1611

    Article  Google Scholar 

  72. Kißener W (1985) PD thesis, University of Bonn

    Google Scholar 

  73. Staab HA, Diederich F (1983) Chem Ber 116: 3487

    Google Scholar 

  74. Grützmacher HF, Husemann W (1987) Tetrahedron 43: 3205

    Article  Google Scholar 

  75. Brudermüller M, Musso H, Wagner A (1988) Chem Ber 121: 2239

    Google Scholar 

  76. Staab HA, Wahl P, Kay KY (1987) Chem Ber 120: 541

    Google Scholar 

  77. Hojjatie M, Mulidharan S, Freiser H (1989) Tetrahedron 45: 1611

    Article  Google Scholar 

  78. Higuchi H, Tani K, Otsubo T, Sakata Y, Misumi S (1987) Bull Chem Soc Jpn 60: 4027

    Google Scholar 

  79. Vögtle F, Ley F (1978) Chem Ber 111: 2445

    Google Scholar 

  80. Papkalla T (1989) PD thesis, University of Bonn

    Google Scholar 

  81. Meurer KP (1984) PD thesis, University of Bonn

    Google Scholar 

  82. Walba DM, Armstrong JD, Perry AE, Richards RM, Homan TC, Haltiwanger RC (1986) Tetrahedron 42: 1883

    Article  Google Scholar 

  83. Walba DM, Richards RM, Hermsmeier M, Haltiwanger RC (1987) J Am Chem Soc 109: 7081

    Article  Google Scholar 

  84. Dijkstra PJ, van Steen BJ, Hams BHM, den Hertog Jr HJ, Reinhoudt DN (1986) Tetrahedron Lett 27: 3183

    Article  Google Scholar 

  85. Cram DJ (1986) Angew Chem 98: 1041; (1986) Angew Chem, Int Ed Engl 25: 1039

    Google Scholar 

  86. Alston DR, Slawin AMZ, Stoddart JF, Williams DJ, Zarzycki R (1987) Angew Chem 99: 697; (1987) Angew Chem, Int Ed Engl 26: 692

    Google Scholar 

  87. Saward E, Diederich F (1987) Tetrahedron Lett 28: 5111

    Article  Google Scholar 

  88. Chambron JC, Sauvage JP (1987) Tetrahedron 43: 895

    Article  Google Scholar 

  89. Marshall JA, Lebreton J, DeHoff BS, Jenson TM (1987) Tetrahedron Lett 28: 723

    Article  Google Scholar 

  90. Dietrich-Buchecker CO, Sauvage JP (1989) Angew Chem 101: 192; (1989) Angew Chem, Int Ed Engl 28: 189

    Google Scholar 

  91. Heinz W, Räder HJ, Müllen K (1989) Tetrahedron Lett 30: 159

    Article  Google Scholar 

  92. Richards TI, Layden K, Warminski EE, Milburn PJ, Haslam E (1987) J Chem Soc, Perkin Trans I 2765

    Google Scholar 

  93. Chen CS, Chao HE, Wang SJ (1987) Synth Commun 17: 1431

    Google Scholar 

  94. van Staveren CJ, Aarts VMLJ, Grootenhuis PDJ, Droppers WJH, van Eerden J, Harkema S, Reinhoudt DN (1988) J Am Chem Soc 110: 8134

    Article  Google Scholar 

  95. Diederich F, Hester MR, Uyeki MA (1988) Angew Chem 100: 1775; (1988) Angew Chem, Int Ed Engl 27: 1705

    Google Scholar 

  96. Bencini A, Bianchi A, Garcia-Espana E, Giusti M, Mangani S, Micheloni M, Orioli P, Paoletti P (1987) Inorg Chem 26: 1243

    Article  Google Scholar 

  97. Bencini A, Bianchi A, Garcia-Espana E, Giusti M, Michelou M, Paoletti P (1987) Inorg Chem 26: 681

    Article  Google Scholar 

  98. Marecek JF, Burrows CJ (1986) Tetrahedron Lett 27: 5943

    Article  Google Scholar 

  99. Zask A, Gonnella N, Nakanishi K, Turner CJ, Imajo S, Nozoe T (1986) Inorg Chem 25: 3400

    Article  Google Scholar 

  100. Odashima K, Itai A, Iitaka Y, Koga K (1980) J Am Chem Soc 102: 2504

    Article  Google Scholar 

  101. Mori K, Odashima K, Itai A, Iitaka Y, Koga K (1984) Heterocycles 21: 388

    Google Scholar 

  102. Hosseini MW, Lehn JM (1987) J Am Chem Soc 109: 7047

    Article  Google Scholar 

  103. Heyer D, Lehn JM (1986) Tetrahedron Lett 27: 5869

    Article  Google Scholar 

  104. Losensky HW, Spelthann H, Ehlen A, Vögtle F, Bargon J (1988) Angew Chem 100: 1225; (1988) Angew Chem, Int Ed Engl 27: 1189

    Google Scholar 

  105. Ebmayer F, Vögtle F (1989) Chem Ber 122: 1725

    Google Scholar 

  106. Vriesema BK, Buter J, Kellogg RM (1984) J Org Chem 49: 110

    Article  Google Scholar 

  107. Hosseini MW, Lehn JM (1986) Helv Chim Acta 69: 587

    Article  Google Scholar 

  108. Dietrich B, Hosseini MW, Lehn JM, Sessions RB (1985) Helv Chim Acta 68: 289

    Article  Google Scholar 

  109. Breslow R, Czarnik AW, Lauer M, Leppkes R, Winkler J, Zimmerman S (1986) J Am Chem Soc 108: 1969

    Article  Google Scholar 

  110. Saigo K, Lin RJ, Kubo M, Youda A, Hasegawa M (1986) Chem Lett 519

    Google Scholar 

  111. Wilcox CS, Cowart MD (1986) Tetrahedron Lett 27: 5563

    Article  Google Scholar 

  112. Jazwinski J, Lehn JM, Lilienbaum D, Ziessel R, Guilhem J, Pascard C (1987) J Chem Soc, Chem Commun 1691

    Google Scholar 

  113. Chang CA, Ochaya VO (1988) J Org Chem 53: 5

    Google Scholar 

  114. Schmidt U, Lieberknecht A, Haslinger E (1985) In: Brossi E (ed) The alcaloids. Academic Press, New York, vol 26, p 299

    Google Scholar 

  115. Larkins HL, Hamilton AD (1986) Tetrahedron Lett 27: 2721

    Google Scholar 

  116. Hamilton AD, Van Engen D (1987) J Am Chem Soc 109: 5035

    Google Scholar 

  117. Hirst SC, Hamilton AD (1990) Tetrahedron Lett 31: 2401

    Google Scholar 

  118. Hamilton AD, Little D (1990) J Chem Soc, Chem Commun 297

    Google Scholar 

  119. Peter-Katalinić J, Ebmeyer F, Seel C, Vögtle F (1989) Chem Ber 122: 2391

    Google Scholar 

  120. Kiggen W, Vögtle F (1984) Angew Chem 96: 712; (1984) Angew Chem, Int Ed Engl 23: 714

    Google Scholar 

  121. Stutte P, Kiggen W, Vögtle F (1987) Tetrahedron 43: 2065

    Google Scholar 

  122. Vögtle F, Müller WM, Werner U, Losensky HW (1987) Angew Chem 99: 930; (1987) Angew Chem, Int Ed Engl 26: 901

    Google Scholar 

  123. Fujita T, Lehn JM (1988) Tetrahedron Lett 29: 1709

    Google Scholar 

  124. Schmidt U (1986) Pure Appl Chem 58: 295

    Google Scholar 

  125. Pastuszak J, Gardner JH, Singh J, Rich DH (1982) J Org Chem 47: 2982

    Google Scholar 

  126. Rothe M, Mästle W (1982) Angew Chem 94: 223; (1982) Angew Chem, Int Ed Engl 21: 220

    Google Scholar 

  127. Schmidt U, Utz R, Lieberknecht A, Griesser H, Potzolli B, Bahr J, Wagner K, Fischer P (1987) Synthesis 233

    Google Scholar 

  128. Baker R, Castro JL (1989) J Chem Soc, Chem Commun 378

    Google Scholar 

  129. Kato S, Hamada Y, Shioiri T (1986) Tetrahedron Lett 27: 2653

    Article  Google Scholar 

  130. Sugiura T, Hamada Y, Shioiri T (1987) Tetrahedron Lett 28: 2251

    Article  Google Scholar 

  131. Evans DA, Ellman JA (1989) J Am Chem Soc 111: 1063

    Article  Google Scholar 

  132. Schmidt U, Kroner M, Griesser H (1988) Tetrahedron Lett 29: 3057

    Article  Google Scholar 

  133. Schmidt U, Weller D (1986) Tetrahedron Lett 27: 3495

    Article  Google Scholar 

  134. Schmidt U, Griesser H, Lieberknecht A, Talbiersky J (1981) Angew Chem 93: 271; (1981) Angew Chem, Int Ed Engl 20: 280

    Google Scholar 

  135. Schmidt U, Lieberknecht A, Griesser H, Talbiersky J (1982) J Org Chem 47: 3261

    Article  Google Scholar 

  136. Schmidt U, Lieberknecht A, Bökens H, Griesser H (1983) J Org Chem 48: 2680

    Article  Google Scholar 

  137. Schmidt U, Schanbacher U (1984) Liebigs Ann Chem 1205

    Google Scholar 

  138. Schmidt U, Bökens H, Lieberknecht A, Griesser H (1983) Liebigs Ann Chem 1459

    Google Scholar 

  139. Schmidt U, Lieberknecht A, Griesser H, Hänsler J (1982) Liebigs Ann Chem 2153

    Google Scholar 

  140. Biernat JF, Bochenska M, Bradshaw JS, Koyama H, Lindk G, Lamb JD, Christensen JJ, Izatt RM (1987) J Incl Phen 5: 729

    Article  Google Scholar 

  141. Nakatsuka S, Masuda T, Sakai K, Goto T (1985) Tetrahedron Lett 26: 5735

    Article  Google Scholar 

  142. Rodgers SJ, Ng CY, Raymond KN (1985) J Am Chem Soc 107: 4094

    Article  Google Scholar 

  143. Werner U, Müller WM, Losensky HW, Merz T, Vögtle F (1986) J Incl Phen 4: 379

    Article  Google Scholar 

  144. Neugebauer FA, Fischer H (1986) Tetrahedron Lett 27: 5367

    Article  Google Scholar 

  145. Murakami Y, Aoyama Y, Kikuchi J, Nishida K (1982) J Am Chem Soc 104: 5189

    Article  Google Scholar 

  146. McMurry TJ, Rodgers SJ, Raymond KN (1987) J Am Chem Soc 109: 3451

    Article  Google Scholar 

  147. Hider RC (1984) Struct Bonding 58: 25

    Google Scholar 

  148. Grammenudi S, Vögtle F (1986) Angew Chem 98: 1119; (1986) Angew Chem, Int Ed Engl 25: 1122

    Google Scholar 

  149. Schurmann G, Diederich F (1986) Tetrahedron Lett 27: 4249

    Article  Google Scholar 

  150. Wallon A, Peter-Katalinić J, Werner U, Müller WM, Vögtle F (1990) Chem Ber 123: 375

    Google Scholar 

  151. Dubowchik GM, Hamilton AD (1986) J Chem Soc, Chem Commun 665

    Google Scholar 

  152. Dubowchik GM, Hamilton AD (1987) J Chem Soc, Chem Commun 293

    Google Scholar 

  153. Collman JP, Chong AO, Jameson GB, Oakley RT, Rose E, Schmittou ER, Ibers JA (1981) J Am Chem Soc 103: 516

    Article  Google Scholar 

  154. Collman JP, Brauman JI, Collins TJ, Iverson BL, Lang G, Pettman RB, Sessler JL, Walters MA (1983) J Am Chem Soc 105: 3038

    Article  Google Scholar 

  155. Wambach L, Vögtle F (1985) Tetrahedron Lett 26: 1483

    Article  Google Scholar 

  156. Ireland C, Scheuer PJ (1980) J Am Chem Soc 102: 5688

    Article  Google Scholar 

  157. Lagarias JC, Houghten RA, Rapoport H (1978) J Am Chem Soc 100: 8202

    Article  Google Scholar 

  158. McMurry TJ, Hosseini MW, Garrett TM, Hahn FE, Reyes ZE, Raymond KN (1987) J Am Chem Soc 109: 7196

    Article  Google Scholar 

  159. Uemori Y, Kyuno E (1987) Inorg Chim Acta 138: 9

    Article  Google Scholar 

  160. Schrage H, Vögtle F, Steckhan E (1988) J Incl Phen 6: 157

    Article  Google Scholar 

  161. Schmidt U, Werner J (1986) Synthesis 986

    Google Scholar 

  162. Rastetter WH, Phillion DP (1981) J Org Chem 46: 3209

    Article  Google Scholar 

  163. Seebach D, Brändli U, Schnurrenberger P, Przybylski M (1988) Helv Chim Acta 71: 155

    Article  Google Scholar 

  164. Maciejewski L, Martin M, Ricart G, Brocard J (1988) Synth Commun 18: 1757

    Google Scholar 

  165. Picard D, Cazaux L, Tisnes P (1986) Tetrahedron 42: 3503

    Article  Google Scholar 

  166. Quinkert G, Heim N, Glenneberg J, Döller U, Eichhorn M, Billhardt UM, Schwarz C, Zimmermann G, Bats JW, Dürner G (1988) Helv Chim Acta 71: 1719

    Article  Google Scholar 

  167. Quinkert G, Heim N, Glenneberg J, Billhardt UM, Autze V, Bats JW, Dürner G (1987) Angew Chem 99: 363; (1987) Angew Chem, Int Ed Engl 26: 362

    Google Scholar 

  168. Wasserman HH, Gambale RJ, Pulwer MJ (1981) Tetrahedron 37: 4059

    Article  Google Scholar 

  169. Quinkert G, Billhardt UM, Jakob H, Fischer G, Glenneberg J, Nagler P, Autze V, Heim N, Wacker M, Schwalbe T, Kurth Y, Nats JW, Dürner G, Zimmermann G, Kessler H (1987) Helv Chim Acta 70: 771

    Article  Google Scholar 

  170. Jolley ST, Bradshaw JS (1980) J Org Chem 45: 3554

    Google Scholar 

  171. Feldman KS, Lee YB (1987) J Am Chem Soc 109: 5850

    Google Scholar 

  172. Miljkovic D, Kuhajda K (1987) Tetrahedron Lett 28: 5737

    Google Scholar 

  173. Schmidt U, Heermann D (1979) Angew Chem 91: 330; (1979) Angew Chem, Int Ed Engl 18: 308

    Google Scholar 

  174. Schmidt U, Werner J (1986) J Chem Soc, Chem Commun 996

    Google Scholar 

  175. Schmidt U, Dietsche M (1981) Angew Chem 93: 786; (1981) Angew Chem, Int Ed Engl 20: 771

    Google Scholar 

  176. Gerlach H, Thalmann A (1974) Helv Chim Acta 57: 2661

    Article  Google Scholar 

  177. Kurihara T, Nakajima Y, Mitsunobu O (1976) Tetrahedron Lett 2455

    Google Scholar 

  178. Bestmann HJ, Schobert R (1985) Angew Chem 97: 784; (1985) Angew Chem, Int Ed Engl 24: 791

    Google Scholar 

  179. Bestmann HJ, Schobert R (1985) Angew Chem 97: 783; (1985) Angew Chem, Int Ed Engl 24: 790

    Google Scholar 

  180. Scott PW, Harrison IT (1981) J Org Chem 46: 1914

    Google Scholar 

  181. Koert U, Fernholz E (1988) Git Fachz Lab 32: 627

    Google Scholar 

  182. Yoshida M, Harada N, Nakamura H, Kanematsu K (1988) Tetrahedron Lett 29: 6129

    Google Scholar 

  183. Cazaux L, Duriez MC, Picard C, Tisnes P (1989) Tetrahedron Lett 30: 1369

    Google Scholar 

  184. Leeper FJ, Smith DHC (1988) Tetrahedron Lett 29: 1325

    Google Scholar 

  185. Leygue N, Picard C, Tisnes P, Cazaux L (1988) Tetrahedron 44: 5845

    Google Scholar 

  186. Mahajan JR, Resck IS (1980) Synth Commun 998

    Google Scholar 

  187. Baker W, Buggle KM, McOmie JFW, Watkins DAM (1958) J Chem Soc 3594

    Google Scholar 

  188. Vögtle F, Körsgen UU, Puff H, Reuter H (1989) Chem Ber 122: 343

    Google Scholar 

  189. Merz T, Wirtz H, Vögtle F (1986) Angew Chem 98: 549; (1986) Angew Chem, Int Ed Engl 25: 567

    Google Scholar 

  190. Casadei MA, Galli C, Mandolini L (1981) J Org Chem 46: 3127

    Google Scholar 

  191. Shinmyozu T, Sakai T, Uno E, Inazu T (1985) J Org Chem 50: 1959

    Google Scholar 

  192. Deslongchamps P, Lamothe S, Lin HS (1987) Can J Chem 65: 1298

    Google Scholar 

  193. Miyahara Y, Inazu T, Yoshino T (1983) Tetrahedron Lett 24: 5277

    Google Scholar 

  194. Park CH, Simmons HE (1972) J Am Chem Soc 94: 7184

    Google Scholar 

  195. Kurosawa K, Suenaga M, Inazu T, Yoshino T (1982) Tetrahedron Lett 23: 5335

    Google Scholar 

  196. Shinmyozu T, Hirai Y, Inazu T (1986) J Org Chem 51: 1551

    Google Scholar 

  197. Wirtz H, Vögtle F, Puff H, Woller P (1986) J Incl Phen 4: 135

    Google Scholar 

  198. Miller SP, Whitlock Jr HW (1984) J Am Chem Soc 106: 1492

    Google Scholar 

  199. Sheridan RE, Whitlock Jr HW (1986) J Am Chem Soc 108: 7120

    Google Scholar 

  200. Ojima J, Fujita S, Masumoto M, Ejiri E, Kato T, Kuroda S, Nozawa Y, Tatemitsu H (1987) J Chem Soc, Chem Commun 534

    Google Scholar 

  201. Ojima J, Ejiri E, Kato T, Kuroda S, Hirooka S, Shibutani M (1986) Tetrahedron Lett 27: 2467

    Google Scholar 

  202. Jarvi ET, Whitlock HW (1982) J Am Chem Soc 104: 7196

    Google Scholar 

  203. Marshall JA, Gung WY (1989) Tetrahedron Lett 30: 309

    Google Scholar 

  204. Brocchini SJ, Eberle M, Lawton RG (1988) J Am Chem Soc 110: 5211

    Google Scholar 

  205. Catoni G, Galli C, Mandolini L (1980) J Org Chem 45: 1906

    Google Scholar 

  206. Morgan B, Dolphin D (1985) Angew Chem 97: 1000; (1985) Angew Chem, Int Ed Engl 24: 1003

    Google Scholar 

  207. Staab HA, Matzke G, Krieger C (1987) Chem Ber 120: 89

    Google Scholar 

  208. Wilcox Jr CF, Weber KA (1986) J Org Chem 51: 1088

    Google Scholar 

  209. Yvergnaux F, Le Floc'h Y, Grée R (1989) Tetrahedron Lett 30: 7397

    Google Scholar 

  210. McMurry JE (1983) Acc Chem Res 16: 405

    Google Scholar 

  211. Ojima J, Yamamoto K, Kato T, Wada K, Yonegawa Y, Ejiri E (1986) Bull Chem Soc Jpn 59: 2209

    Google Scholar 

  212. Vogel E, Püttmann W, Duchatsch W, Schieb T, Schmickler H, Lex J (1986) Angew Chem 98: 727; (1986) Angew Chem, Int Ed Engl 25: 720

    Google Scholar 

  213. McMurry JE, Haley GJ, Matz JR, Clardy JC, Duyne GV, Gleiter R, Schäfer W, White DH (1986) J Am Chem Soc 108: 2932

    Google Scholar 

  214. Yamamoto K, Shibutani M, Kuroda S, Ejiri E, Ojima J (1986) Tetrahedron Lett 27: 975

    Google Scholar 

  215. McMurry JE, Matz JR, Kees KL (1987) Tetrahedron 43: 5489

    Google Scholar 

  216. McMurry JE, Haley GJ, Matz JR, Clardy JC, Mitchell J (1986) J Am Chem Soc 108: 515

    Google Scholar 

  217. Herin M, Colin M, Tursch B (1976) Bull Soc Chim Belges 85: 801

    Google Scholar 

  218. Stork G, Nakamura E (1979) J Org Chem 44: 4010

    Google Scholar 

  219. Raddatz P, Winterfeldt E (1981) Angew Chem 93: 281; (1981) Angew Chem, Int Ed Engl 20: 286

    Google Scholar 

  220. Nicolaou KC, Chakraborty TK, Daines RA, Simpkins NS (1986) J Chem Soc, Chem Commun 413

    Google Scholar 

  221. Nicolaou KC, Daines RA, Chakraborty TK (1987) J Am Chem Soc 109: 2208

    Google Scholar 

  222. Bailey SJ, Thomas EJ, Vather SM, Wallis J (1983) J Chem Soc, Perkin I 851

    Google Scholar 

  223. Eberbach W, Heinze I, Knoll K, Fritz H, Borle F (1988) Helv Chim Acta 71: 404

    Google Scholar 

  224. Juriew J, Skorochodowa T, Merkuschew J, Winter W, Meier H (1981) Angew Chem 93: 285; (1981) Angew Chem, Int Ed Engl 20: 269

    Google Scholar 

  225. Scott PW, Harrison IT (1981) J Org Chem 46: 1914

    Google Scholar 

  226. Baldwin JE, Adlington RM, Robertson J (1989) Tetrahedron 45: 909

    Google Scholar 

  227. Vagt U, Haase M, Konusch J, Tochtermann W (1987) Chem Ber 120: 769

    Google Scholar 

  228. Raasch MS (1979) J Org Chem 44: 2629

    Google Scholar 

  229. Houk J, Whitesides GM (1989) Tetrahedron 45: 91

    Google Scholar 

  230. Regen SL, Kimura Y (1982) J Am Chem Soc 104: 2064

    Google Scholar 

  231. Trost BM, Warner RW (1982) J Am Chem Soc 104: 6112

    Article  Google Scholar 

  232. Kimura Y, Regen SL (1983) J Org Chem 48: 1533

    Google Scholar 

  233. Gonzalez A, Holt SL (1981) J Org Chem 46: 2594

    Google Scholar 

  234. Singh P, Jain A (1988) Inidian J Chem, Sect B 27: 937

    Google Scholar 

  235. Singh H, Kumar M, Singh P, Kumar S (1988) J Chem Res (S) 132

    Google Scholar 

  236. Singh H, Kumar M, Singh P (1989) J Chem Res (S) 94; (1989) ibid (M) 0675

    Google Scholar 

  237. Geuder W, Hünig S, Suchy A (1983) Angew Chem 95: 501; (1983) Angew Chem, Int Ed Engl 22: 489

    Google Scholar 

  238. Geuder W, Hünig S, Suchy A (1986) Tetrahedron 42: 1665

    Google Scholar 

  239. Schneider HJ, Busch R (1986) Chem Ber 119: 747

    Google Scholar 

  240. Jurczak J, Ostazewski R, Salanski P (1989) J Chem Soc, Chem Commun 184

    Google Scholar 

  241. Kohnke FH, Slawin AMZ, Stoddart JF, Williams DJ (1987) Angew Chem 99: 941; (1987) Angew Chem, Int Ed Engl 26: 892

    Google Scholar 

  242. Kohnke FH, Mathias JP, Stoddart JF (1989) Angew Chem Adv Mater 101: 1129; (1989) Angew Chem, Int Ed Engl 28: 1103

    Google Scholar 

  243. Ashton PR, Isaacs NS, Kohnke FH, Stagno d'Alcontres G, Stoddart JF (1989) Angew Chem 101: 1269; (1989) Angew Chem, Int Ed Engl 28: 1261

    Google Scholar 

  244. Ashton PR, Goodnow TT, Kaifer AE, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1989) Angew Chem 101: 1404; (1989) Angew Chem, Int Ed Engl 28: 1396

    Google Scholar 

  245. Bühner M, Geuder W, Gries WK, Hünig S, Koch M, Poll T (1988) Angew Chem 100: 1611; (1989) Angew Chem, Int Ed Engl 27: 1553

    Google Scholar 

  246. The authors kindly thank Prof. Stoddart for his permission to use drawings of the molecules 123–128

    Google Scholar 

  247. Rodriguez-Ubis JC, Alpha B, Plancherel D, Lehn JM (1984) Helv Chim Acta 67: 2264

    Google Scholar 

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Knops, P., Sendhoff, N., Mekelburger, HB., Vögtle, F. (1992). High dilution reactions — New synthetic applications. In: Macrocycles. Topics in Current Chemistry, vol 161. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-54348-1_6

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