What is New in [2.2]Paracyclophane Chemistry?

Synlett

Volumn 1997, Issue 11, 1997, Pages 1221-1232

  De Meijere, Armin ^{a,b,c,d,e,f,g,h,i,j,k,l,m,n}   König, Burkhard ^b,d,o,p  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^c YALE UNIVERSITY   (United States)

^d UNIVERSITY OF HAMBURG   (Germany)

^e UNIVERSITY OF WISCONSIN MADISON   (United States)

^f IBM ALMADEN RESEARCH CENTER   (United States)

^g TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^h PRINCETON UNIVERSITY   (United States)

ⁱ AIX MARSEILLE UNIVERSITY   (France)

^j UNIVERSITY OF FLORENCE   (Italy)

^k ECOLE NORMALE SUPÉRIEURE   (France)

^l Det Norske Videnskaps Akademi   (Norway)

^m French Ministery Higher Educ Res   (France)

ⁿ JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

^o AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^p STANFORD UNIVERSITY   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2342526051     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1000     Document Type: Article

References (104)

1. (a) Pellegrin, M. M. Rec. Trav. Chim. Pays-Bas 1899, 18, 457-465;
2. (b) Brown, C. J.; Farthing, A. C. Nature 1949, 164, 915-916.
3. (a) Keehn, P. M., Rosenfeld, S. M. Cyclophanes, I, II. Academic Press, New York, 1983;
4. (b) Vögtle, F. Cyclophane Chemistry, Wiley, New York, 1993;
5. (c) for a recent highlight on cyclophane chemistry in general see: Bodwell, G. J. Angew. Chem. 1996, 108, 2221-2224; Angew. Chem. Int. Ed. Engl. 1996, 35, 2085-2088.
6. (c) for a recent highlight on cyclophane chemistry in general see: Bodwell, G. J. Angew. Chem. 1996, 108, 2221-2224; Angew. Chem. Int. Ed. Engl. 1996, 35, 2085-2088.
7. Cf. Atwood, J. L.; Davies, J. E. D.; Macnicol, D. D.; Vögtle, F.; Lehn, J.-M., Eds. Comprehensive Supramolecular Chemistry, Vol. 1, 2 and 10, Elsevier Science, Oxford, 1996.
8. (a) Gutsche, C. D. Calixarenes; Monographs in Supramolecular Chemistry, Stoddart, J. F., Ed.; The Royal Society of Chemistry, London, 1989;
9. (b) Vögtle, F. Supramolecular Chemistry, Wiley, New York, 1992;
10. (c) recent example: Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M. Nature, 1996 382, 522-524.
11. (a) Wegner, G. Angew. Chem. 1981, 93, 352-371; Angew. Chem. Int. Ed. Engl. 1981, 20, 361-381;
12. (a) Wegner, G. Angew. Chem. 1981, 93, 352-371; Angew. Chem. Int. Ed. Engl. 1981, 20, 361-381;
13. (b) Hanack, M. Nachr. Chem. Tech. Lab. 1980, 28, 632-636.
14. (a) Chan, C. W.; Wong, H. N. C. J. Am. Chem. Soc. 1988, 110, 462-469;
15. (b) Chan, C. W.; Wong, H. N. C. J. Am. Chem. Soc. 1985, 707, 4790-4791.
16. Reiser, O.; Reichow, S.; de Meijere, A. Angew. Chem. 1987, 99, 1285-1286; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277-1278. The overall yields of 6 and 7 can be improved by separating the mixture of 4/5 first and subjecting each one to the sequence of bromination/dehydrobromination. Rauch, K; de Meijere, A. unpublished results.
17. Reiser, O.; Reichow, S.; de Meijere, A. Angew. Chem. 1987, 99, 1285-1286; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277-1278. The overall yields of 6 and 7 can be improved by separating the mixture of 4/5 first and subjecting each one to the sequence of bromination/dehydrobromination. Rauch, K; de Meijere, A. unpublished results.
18. Reiser, O.; Reichow, S.; de Meijere, A. Angew. Chem. 1987, 99, 1285-1286; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277-1278. The overall yields of 6 and 7 can be improved by separating the mixture of 4/5 first and subjecting each one to the sequence of bromination/dehydrobromination. Rauch, K; de Meijere, A. unpublished results.
19. Reiser, O.; König, B.; Meerholz, K.; Heinze, J.; Wellauer, T.; Gerson, F.; Frim, R.; Rabinovitz, M.; de Meijere, A. J. Am. Chem. Soc. 1993, 115, 3511-3518.
20. König, B.; de Meijere, A. Chem. Ber. 1992, 125, 1895-1898.
21. Blatter, K.; Schlüter, A.-D.; Wegner, G. J. Org. Chem. 1989, 54, 2396-2401.
22. (a) Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691-5704;
23. (b) Bruhin, J.; Gerson, F.; Möckel, R.; Plattner, G. Helv. Chim. Acta 1985, 68, 377-390;
24. (c) Otsubo, T.; Boekelheide, V. J. Org. Chem. 1977, 42, 1085-1087;
25. (d) Stöbbe, M.; Reiser, O.; Näder, R.; de Meijere, A. Chem. Ber. 1987, 120, 1667-1674.
26. König, B.; Heinze, J.; Meerholz, K.; de Meijere, A. Angew. Chem. 1991, 103, 1350-1351; Angew. Chem. Int. Ed. Engl. 1991, 30, 1361-1362.
27. König, B.; Heinze, J.; Meerholz, K.; de Meijere, A. Angew. Chem. 1991, 103, 1350-1351; Angew. Chem. Int. Ed. Engl. 1991, 30, 1361-1362.
28. (a) Hart, H.; Lai, C.; Nwokogu, G. C.; Shamouilian, S. Tetrahedron 1987, 43, 5203-5224;
29. (b) Hart, H.; Bashir-Hashemi, A.; Luo, J.; Meador, M. A. Tetrahedron 1986, 42, 1641-1654.
30. Blatter, K.; Schlüter, A.-D. Chem. Ber. 1989, 122, 1351-1356.
31. Cf. Krasovitskii, B. M.; Bolotin, B. M. Organic Luminescent Materials, VCH, Weinheim, 1988, p. 277.
32. de Meijere, A.; Heinze, J.; Meerholz, K.; Reiser, O.; König, B. Angew. Chem. 1990, 102, 1443-1445; Angew. Chem. Int. Ed. Engl. 1990, 29, 1418-1419.
33. de Meijere, A.; Heinze, J.; Meerholz, K.; Reiser, O.; König, B. Angew. Chem. 1990, 102, 1443-1445; Angew. Chem. Int. Ed. Engl. 1990, 29, 1418-1419.
34. Psiorz, M.; Hopf, H. Angew. Chem. 1982, 94, 639-640; Angew. Chem. Int. Ed. Engl. 1982, 21, 623-624.
35. Psiorz, M.; Hopf, H. Angew. Chem. 1982, 94, 639-640; Angew. Chem. Int. Ed. Engl. 1982, 21, 623-624.
36. (a) Albrecht, K.; de Meijere, A. Chem. Ber. 1994, 127, 2539-2541;
37. (b) de Meijere, A.; Rauch, K.; Noltemeyer, M.; Knieriem, B.; Albrecht, K.; Hopf, H., unpublished results.
38. Gerson, F.; Scholz, M.; de Meijere, A.; König, B.; Heinze, J.; Meerholz, K. Helv. Chim. Acta. 1992, 75, 2307-2316.
39. (a) Dewhirst, K. C.; Cram, D. J. J. Am. Chem. Soc. 1958, 80, 3115-3125; (b) For improved procedures for the synthesis of 32 and 42 see ref. 11d.
40. (a) Hopf, H.; Psiorz, M. Chem. Ber. 1986, 119, 1836-1844;
41. (b) Raasch, M. S. J. Org. Chem. 1980, 45, 856-867.
42. Taylor, E. C.; Ehrhart, W. A. J. Am. Chem. Soc. 1960, 82, 3138-3141.
43. Beck, K.; Höhn, A.; Hünig, S.; Prokschy, F. Chem. Ber. 1984, 117, 517-533.
44. Bennett, M. A.; Schwemlein, H. P. Angew. Chem. 1989, 101, 1349-1373; Angew. Chem. Int. Ed. Engl. 1989, 28, 1296-1320.
45. Bennett, M. A.; Schwemlein, H. P. Angew. Chem. 1989, 101, 1349-1373; Angew. Chem. Int. Ed. Engl. 1989, 28, 1296-1320.
46. (a) Buchwald, S. L.; Lum, R. T.; Dewan, J. C. J. Am. Chem. Soc. 1986, 108, 7441-7442;
47. (b) Barr, K. J.; Watson, B. T.; Buchwald, S. L. Tetrahedron Lett. 1991, 32, 5465-5468.
48. König, B.; Bennett, M. A.; de Meijere, A. Synlett 1994, 653-654.
49. Albrecht, K.; Hockless, D. C. R.; König, B.; Neumann, H.; Bennett, M. A.; de Meijere, A. J. Chem. Soc. Chem. Commun. 1996, 543-544.
50. (a) de Meijere, A.; Reiser, O.; Stöbbe, M.; Kopf, J.; Adiwidjaja, G.; Sinnwell, V.; Khan, S. I. Acta Chem. Scand. 1988, A42, 611-625;
51. (b) A detailed study of the site selectivity of tricarbonylchromium coordination on substituted [2.2]paracyclophane derivatives has been performed by Rozenberg, V.; Academy of Science, Moscow. Rozenberg, L.; personal communication.
52. Frim, R.; Raulfs, F.-W.; Hopf, H.; Rabinovitz, M. Angew. Chem. 1986, 98, 160-161; Angew. Chem. Int. Ed. Engl. 1986, 25, 174-175; for the synthesis of [2]metacyclo[2]indenophanes, see: Bodwell, G. J.; Frim, R.; Hopf, H.; Rabinovitz, M. Chem. Ber. 1993, 120, 167-175.
53. Frim, R.; Raulfs, F.-W.; Hopf, H.; Rabinovitz, M. Angew. Chem. 1986, 98, 160-161; Angew. Chem. Int. Ed. Engl. 1986, 25, 174-175; for the synthesis of [2]metacyclo[2]indenophanes, see: Bodwell, G. J.; Frim, R.; Hopf, H.; Rabinovitz, M. Chem. Ber. 1993, 120, 167-175.
54. Frim, R.; Raulfs, F.-W.; Hopf, H.; Rabinovitz, M. Angew. Chem. 1986, 98, 160-161; Angew. Chem. Int. Ed. Engl. 1986, 25, 174-175; for the synthesis of [2]metacyclo[2]indenophanes, see: Bodwell, G. J.; Frim, R.; Hopf, H.; Rabinovitz, M. Chem. Ber. 1993, 120, 167-175.
55. Frim, R.; Rabinovitz, M.; Bodwell, G.; Raulfs, F.-W.; Hopf, H. Chem. Ber. 1989, 122, 737-744.
56. Hopf, H.; Dannheim, J. Angew. Chem. 1988, 100, 724-725; Angew. Chem. Int. Ed. Engl. 1988, 27, 701.
57. Hopf, H.; Dannheim, J. Angew. Chem. 1988, 100, 724-725; Angew. Chem. Int. Ed. Engl. 1988, 27, 701.
58. de Meijere, A.; Höfer, J.; Buchholz, H.; König, B. unpublished results. Höfer, J. Dissertation, Universität Hamburg, 1989; Buchholz, H. Dissertation, Universität Hamburg, 1992; König, B. Dissertation, Universität Hamburg, 1991.
59. de Meijere, A.; Höfer, J.; Buchholz, H.; König, B. unpublished results. Höfer, J. Dissertation, Universität Hamburg, 1989; Buchholz, H. Dissertation, Universität Hamburg, 1992; König, B. Dissertation, Universität Hamburg, 1991.
60. de Meijere, A.; Höfer, J.; Buchholz, H.; König, B. unpublished results. Höfer, J. Dissertation, Universität Hamburg, 1989; Buchholz, H. Dissertation, Universität Hamburg, 1992; König, B. Dissertation, Universität Hamburg, 1991.
61. Buchholz, H.; de Meijere, A. unpublished results; Buchholz, H. Dissertation, Universität Hamburg, 1992.
62. Reviews see: Pauson, P. L. Tetrahedron 1985, 41, 5855-5860; Schore, N. E. Chem. Rev. 1988, 88, 1081-1119; Schore, N. E. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon Press, Oxford 1991, Vol. 5, p. 1037-1064.
63. Reviews see: Pauson, P. L. Tetrahedron 1985, 41, 5855-5860; Schore, N. E. Chem. Rev. 1988, 88, 1081-1119; Schore, N. E. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon Press, Oxford 1991, Vol. 5, p. 1037-1064.
64. Reviews see: Pauson, P. L. Tetrahedron 1985, 41, 5855-5860; Schore, N. E. Chem. Rev. 1988, 88, 1081-1119; Schore, N. E. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon Press, Oxford 1991, Vol. 5, p. 1037-1064.
65. Buchholz, H.; Reiser, O.; de Meijere, A. Synlett 1991, 1, 20-22.
66. Cf. Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. Angew. Chem. 1995, 107, 1255-1283; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143-1170, and references cited therein.
67. Cf. Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. Angew. Chem. 1995, 107, 1255-1283; Angew. Chem. Int. Ed. Engl. 1995, 34, 1143-1170, and references cited therein.
68. (a) Tsuji, T.; Ohkita, M.; Nishida, S. J. Am. Chem. Soc. 1993, 115, 5284-5285;
69. (b) Tsuji, T. unpublished results; personal communication to A. de Meijere, Nov. 1996.
70. Buchholz, H.; de Meijere, A. Synlett 1993, 4, 253-255.
71. Förster, T. Angew. Chem. 1969, 81, 364-374; Angew. Chem. Int. Ed. Engl. 1969, 8, 333-343.
72. Förster, T. Angew. Chem. 1969, 81, 364-374; Angew. Chem. Int. Ed. Engl. 1969, 8, 333-343.
73. Method adopted from: Fieser, L. F.; Haddadin, M. J. Can. J. Chem. 1965, 43, 1599-1606.
74. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667-2670; Tetrahedron 1996, 52, 10113-10130.
75. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667-2670; Tetrahedron 1996, 52, 10113-10130.
76. (a) König, B.; Knieriem, B.; de Meijere, A. Chem. Ber. 1993, 126, 1643-1650;
77. (b) Shabtai, E.; Rabinovitz, M.; König, B.; Knieriem, B.; de Meijere, A. J. Chem. Soc. Perkin Trans. II 1996, 2589-2595.
78. Method adopted from: Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752-755.
79. Krasovitskii, B. M.; Bolotin, B. M. Organic Luminescent Materials, VCH, Weinheim, 1988, p. 41-50.
80. Cohen, M. D.; Schmidt, G. M. J.; Sonntag, F. I. J. Chem. Soc. 1964, 2000-2013.
81. Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J.-P.; Bouas-Laurent, H. J. Chem. Soc. Chem. Commun. 1994, 1075-1076.
82. Hopf, H.; Greiving, H.; Jones, P. G.; Bubenitschek, P. Angew. Chem. 1995, 107, 742-744; Angew. Chem. Int. Ed. Engl. 1995, 34, 685-687; Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J.-P.; Bouas-Laurent, H. Liebigs Ann. 1995, 1949-1956.
83. Hopf, H.; Greiving, H.; Jones, P. G.; Bubenitschek, P. Angew. Chem. 1995, 107, 742-744; Angew. Chem. Int. Ed. Engl. 1995, 34, 685-687; Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J.-P.; Bouas-Laurent, H. Liebigs Ann. 1995, 1949-1956.
84. Hopf, H.; Greiving, H.; Jones, P. G.; Bubenitschek, P. Angew. Chem. 1995, 107, 742-744; Angew. Chem. Int. Ed. Engl. 1995, 34, 685-687; Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J.-P.; Bouas-Laurent, H. Liebigs Ann. 1995, 1949-1956.
85. (a) Nishimura, J. in Carbocyclic Cage Compounds: Chemistry and Applications, Osawa, E.; Yonemitsu, O., Eds.; VCH, New York, 1992, pp 155-181;
86. (b) Nishimura, J.; Okada, Y.; Inokuma, S.; Nakamura, Y.; Gao, S. R. Synlett 1994, 884-894;
87. (c) Nishimura, J.; Doi, H.; Ueda, E.; Ohbayashi, A.; Oku, A. J. Am. Chem. Soc. 1987, 109, 5293-5295.
88. (a) Meier, H.; Müller, K. Angew. Chem. 1995, 107, 1598-1600; Angew. Chem. Int. Ed. Engl. 1995, 34, 1437-1439;
89. (a) Meier, H.; Müller, K. Angew. Chem. 1995, 107, 1598-1600; Angew. Chem. Int. Ed. Engl. 1995, 34, 1437-1439;
90. (b) Meier, H., Angew. Chem. 1992, 104, 1425-1446; Angew. Chem. Int. Ed. Engl. 1992, 31, 1399-1420;
91. (b) Meier, H., Angew. Chem. 1992, 104, 1425-1446; Angew. Chem. Int. Ed. Engl. 1992, 31, 1399-1420;
92. (c) Müller, K.; Meier, H.; Bouas-Laurent, H.; Desvergne, J. P. J. Org. Chem. 1996, 61, 5474-5480.
93. (a) Ashton, P. R.; Isaacs, N. S.; Kohnke, F. H.; Mathias, J. P.; Stoddart, J. F. Angew. Chem. 1989, 101, 1266-1269; Angew. Chem. Int. Ed. Engl. 1989, 28, 1258-1261;
94. (a) Ashton, P. R.; Isaacs, N. S.; Kohnke, F. H.; Mathias, J. P.; Stoddart, J. F. Angew. Chem. 1989, 101, 1266-1269; Angew. Chem. Int. Ed. Engl. 1989, 28, 1258-1261;
95. (b) Ashton, P. R.; Isaacs, N. S.; Kohnke, F. H.; Stagno d'Alcontres, G.; Stoddart, J. F. Angew. Chem. 1989, 101, 1269-1271; Angew. Chem. Int. Ed. Engl. 1989, 28, 1261-1264.
96. (b) Ashton, P. R.; Isaacs, N. S.; Kohnke, F. H.; Stagno d'Alcontres, G.; Stoddart, J. F. Angew. Chem. 1989, 101, 1269-1271; Angew. Chem. Int. Ed. Engl. 1989, 28, 1261-1264.
97. Blatter, K.; Schlüter, A.-D. Macromolecules 1989, 22, 3506-3508.
98. Blatter, K.; Schlüter, A.-D. Chem. Ber. 1989, 122, 1351-1356.
99. König, B.; de Meijere, A.; Schlüter, A.-D. unpublished results.
100. Elschenbroich, C.; Möckel, R.; Zenneck, U. Angew. Chem. 1978, 90, 560-561; Angew. Chem. Int. Ed. Engl. 1978, 17, 531-532.
101. Elschenbroich, C.; Möckel, R.; Zenneck, U. Angew. Chem. 1978, 90, 560-561; Angew. Chem. Int. Ed. Engl. 1978, 17, 531-532.
102. Stöbbe, M. Dissertation, Universität Hamburg, 1986.
103. Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon, Yu. Angew. Chem. 1994, 106, 106-108; Angew. Chem. Int. Ed. Engl. 1994, 33, 91-92.
104. Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon, Yu. Angew. Chem. 1994, 106, 106-108; Angew. Chem. Int. Ed. Engl. 1994, 33, 91-92.