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1
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0004146786
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The Royal Society of Chemistry, Cambridge, England
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For a fascinating review on the development of calixarene chemistry see: C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, England 1989.
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(1989)
Calixarenes
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Gutsche, C.D.1
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2
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0000948055
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For a more recent review see: V. Böhmer, Angew. Chem. 1995, 107, 785-818;
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Angew. Chem.
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Böhmer, V.1
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4
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0000111978
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V. Böhmer, P. Chhim, H. Kämmerer, Makromol. Chem. 1979, 180, 2503-2506.
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Makromol. Chem.
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Böhmer, V.1
Chhim, P.2
Kämmerer, H.3
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5
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0000346504
-
Phenol - Formaldehyde Polymers
-
Pergamon Press
-
Condensation of hydroxymethylated phenols may lead to dibenzyl ether structures (by elimination of water) which can be further converted into methylene bridges (by elimination of formaldehyde). This formally corresponds to electrophilic ipso substitution (compare with A. Knop, V. Böhmer, L. A. Pilato, Phenol - Formaldehyde Polymers, in Comprehensive Polymer Science, Vol. 5, Pergamon Press, 1989).
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(1989)
Comprehensive Polymer Science
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Knop, A.1
Böhmer, V.2
Pilato, L.A.3
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6
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37049082237
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V. Böhmer, L. Merkel, U. Kunz, J. Chem. Soc., Chem. Commun. 1987, 896-897.
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J. Chem. Soc., Chem. Commun.
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Böhmer, V.1
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7
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33845282082
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V. Böhmer, F. Marschollek, L. Zetta, J. Org. Chem. 1987, 52, 3200-3205.
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J. Org. Chem.
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Böhmer, V.1
Marschollek, F.2
Zetta, L.3
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8
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0025978105
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L. Zetta, A. Wolff, W. Vogt, K.-L. Platt, V. Böhmer, Tetrahedron 1991, 47, 1911-1924.
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Tetrahedron
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Zetta, L.1
Wolff, A.2
Vogt, W.3
Platt, K.-L.4
Böhmer, V.5
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9
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0006022174
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J. de Mendoza, P. M. Nieto, P. Prados, C. Sanchez, Tetrahedron 1990, 46, 671-682.
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De Mendoza, J.1
Nieto, P.M.2
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11
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0028842782
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K. No, J. E. Kim, K. M. Kwon, Tetrahedron Lett. 1995, 36, 8453-8456.
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Tetrahedron Lett.
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No, K.1
Kim, J.E.2
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12
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18444399687
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K. No, K. M. Kwon, J. E. Kim, Bull. Korean Chem. Soc. 1996, 17, 525-528.
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Bull. Korean Chem. Soc.
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No, K.1
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13
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0025292858
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M. Tabatabai, W. Vogt, V. Böhmer, Tetrahedron Lett. 1990, 31, 3295-3298.
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(1990)
Tetrahedron Lett.
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, pp. 3295-3298
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Tabatabai, M.1
Vogt, W.2
Böhmer, V.3
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14
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33748822825
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M. Backes, V. Böhmer, G. Ferguson, C. Grüttner, C. Schmidt, W. Vogt, K. Ziat, J. Chem. Soc., Perkin Trans 2, 1997, 1195-1200.
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J. Chem. Soc., Perkin Trans 2
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Backes, M.1
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Grüttner, C.4
Schmidt, C.5
Vogt, W.6
Ziat, K.7
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15
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-
33845376938
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Compare: M. M. Olmstead, G. Sigel, H. Hope, X. Xu, P. P. Power, J. Am. Chem. Soc. 1985, 107, 8087-8091;
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J. Am. Chem. Soc.
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Olmstead, M.M.1
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Xu, X.4
Power, P.P.5
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16
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0027504554
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X. Delaigue, M. W. Hosseini, E. Leize, S. Kiefer, A. Van Dorsselaer, Tetrahedron Lett. 1993, 47, 7561-7564.
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Delaigue, X.1
Hosseini, M.W.2
Leize, E.3
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Van Dorsselaer, A.5
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17
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0000913945
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V. Böhmer, K. Jung, M. Schön, A. Wolff, J. Org. Chem. 1992, 57, 790-792.
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J. Org. Chem.
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Böhmer, V.1
Jung, K.2
Schön, M.3
Wolff, A.4
-
18
-
-
33748811497
-
-
unpublished
-
During the attempted synthesis of alkanediyl bridged calix[5]arenes, for instance, calix[8]arenes were isolated as a side-product or even as the only defined product (C. Grüttner, V. Böhmer, unpublished).
-
-
-
Grüttner, C.1
Böhmer, V.2
-
19
-
-
33748815040
-
-
note
-
[70].
-
-
-
-
20
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0001606803
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S. Pappalardo, G. Ferguson, J. F. Gallagher, J. Org. Chem. 1992, 57, 7102-7109.
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J. Org. Chem.
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Pappalardo, S.1
Ferguson, G.2
Gallagher, J.F.3
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21
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0029086448
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T. Haino, T. Harano, K. Matsumura, Y. Fukazawa, Tetrahedron Lett. 1995, 36, 5793-5796.
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(1995)
Tetrahedron Lett.
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Haino, T.1
Harano, T.2
Matsumura, K.3
Fukazawa, Y.4
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23
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0026644560
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Y. Fukazawa, K. Deyama, S. Usui, Tetrahedron Lett. 1992, 33, 5803-5806.
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(1992)
Tetrahedron Lett.
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, pp. 5803-5806
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Fukazawa, Y.1
Deyama, K.2
Usui, S.3
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24
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0030024780
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Y. Fukazawa, K. Yoshimura, S. Sasaki, M. Yamazaki, T. Okajima, Tetrahedron, 1996, 52, 2301-2318.
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(1996)
Tetrahedron
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, pp. 2301-2318
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Fukazawa, Y.1
Yoshimura, K.2
Sasaki, S.3
Yamazaki, M.4
Okajima, T.5
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25
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0027131751
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S. Usui, K. Deyama, R. Kinoshita, Y. Odagaki, Y. Fukazawa, Tetrahedron Lett. 1993, 34, 8127-8130.
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(1993)
Tetrahedron Lett.
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, pp. 8127-8130
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Usui, S.1
Deyama, K.2
Kinoshita, R.3
Odagaki, Y.4
Fukazawa, Y.5
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26
-
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0028145111
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C. Grüttner, V. Böhmer, W. Vogt, I. Thondorf, S. E. Biali und F. Grynszpan, Tetrahedron Lett. 1994, 35, 6267-6270.
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(1994)
Tetrahedron Lett.
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Grüttner, C.1
Böhmer, V.2
Vogt, W.3
Thondorf, I.4
Biali, S.E.5
Grynszpan, F.6
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27
-
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0030450615
-
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S. E. Biali, V. Böhmer, S. Cohen, G. Ferguson, C. Grüttner, F. Grynszpan, E. F. Paulus, I. Thondorf, W. Vogt, J. Am. Chem. Soc. 1996, 118, 12938-12949.
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J. Am. Chem. Soc.
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Biali, S.E.1
Böhmer, V.2
Cohen, S.3
Ferguson, G.4
Grüttner, C.5
Grynszpan, F.6
Paulus, E.F.7
Thondorf, I.8
Vogt, W.9
-
28
-
-
33748824380
-
-
note
-
Compounds with two adjacent CHR bridges are available analogously by (3 + 1) fragment condensation; unpublished results.
-
-
-
-
29
-
-
3142604993
-
-
See also: V. Böhmer, G. Ferguson, C. Grüttner, W. Vogt, Acta Cryst. 1997, C53, 469-472.
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(1997)
Acta Cryst.
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Böhmer, V.1
Ferguson, G.2
Grüttner, C.3
Vogt, W.4
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30
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-
0000432291
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Y. Ohba, K. Irie, F. S. Zhang, T. Sone, Bull. Chem. Soc. Jpn. 1993, 66, 828-835.
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(1993)
Bull. Chem. Soc. Jpn.
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Ohba, Y.1
Irie, K.2
Zhang, F.S.3
Sone, T.4
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31
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0030581407
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K. Ito, S. Izawa, T. Ohba, Y. Ohba, T. Sone, Tetrahedron Lett. 1996, 37, 5959-5962.
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(1996)
Tetrahedron Lett.
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Ito, K.1
Izawa, S.2
Ohba, T.3
Ohba, Y.4
Sone, T.5
-
32
-
-
33748814134
-
-
private communication
-
Molecular mechanics calculations suggest, however, that the molecules do not assume the cone conformation which has a much higher energy than a distorted partial cone conformation with a helical arrangement of the intramolecular hydrogen bonds. (I. Thondorf, private communication).
-
-
-
Thondorf, I.1
-
33
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-
21844493712
-
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For a recent review see: V. Böhmer, D. Kraft, M. Tabatabai, J. Ind. Phenom. Mol. Recogn. 1994, 19, 17-39.
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(1994)
J. Ind. Phenom. Mol. Recogn.
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Böhmer, V.1
Kraft, D.2
Tabatabai, M.3
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34
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0344254323
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See also: K. No, J. E. Kim, S. J. Kim, Bull. Korean Chem. Soc. 1996, 17, 869-872.
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(1996)
Bull. Korean Chem. Soc.
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No, K.1
Kim, J.E.2
Kim, S.J.3
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35
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0000497294
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For the first examples see: H. Casablanca, J. Royer, A. Satrallah, A. Taty-C, J. Vicens, Tetrahedron Lett. 1987, 28, 6595-6598.
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(1987)
Tetrahedron Lett.
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Casablanca, H.1
Royer, J.2
Satrallah, A.3
Taty-C, A.4
Vicens, J.5
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36
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37049070557
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S. Shinkai, T. Arimura, H. Kawabata, H. Murakami, K. Araki, K. Iwamoto, T. Matsuda, J. Chem. Soc., Chem. Commun. 1990, 1734-1736;
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(1990)
J. Chem. Soc., Chem. Commun.
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Shinkai, S.1
Arimura, T.2
Kawabata, H.3
Murakami, H.4
Araki, K.5
Iwamoto, K.6
Matsuda, T.7
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37
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37049075660
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S. Shinkai, T. Arimura, H. Kawabata, H. Murakami, K. Iwamoto, J. Chem. Soc., Perkin Trans. 1 1991, 2429-2434.
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J. Chem. Soc., Perkin Trans. 1
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Shinkai, S.1
Arimura, T.2
Kawabata, H.3
Murakami, H.4
Iwamoto, K.5
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38
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33751554625
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A. Wolff, V. Böhmer, W. Vogt, F. Ugozzoli, G. D. Andreetti, J. Org. Chem. 1990, 55, 5665-5667.
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J. Org. Chem.
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Wolff, A.1
Böhmer, V.2
Vogt, W.3
Ugozzoli, F.4
Andreetti, G.D.5
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39
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33751386559
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G. D. Andreetti, V. Böhmer, J. G. Jordan, M. Tabatabai, F. Ugozzoli, W. Vogt, A. Wolff, J. Org. Chem. 1993, 58, 4023-4032.
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J. Org. Chem.
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Andreetti, G.D.1
Böhmer, V.2
Jordan, J.G.3
Tabatabai, M.4
Ugozzoli, F.5
Vogt, W.6
Wolff, A.7
-
40
-
-
0000301747
-
-
3, however, gave the same achiral calix[4]arene as was obtained from 2,4-dimethyl-6-hydroxybenzyl alcohol: E. Dahan, S. E. Biali, J. Org. Chem. 1991, 56, 7269-7274.
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J. Org. Chem.
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Dahan, E.1
Biali, S.E.2
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0001100506
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D.-K. Fu, B. Xu, T. M. Swager, J. Org. Chem. 1996, 61, 802-804.
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J. Org. Chem.
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Fu, D.-K.1
Xu, B.2
Swager, T.M.3
-
42
-
-
33748821621
-
-
note
-
For example: for an asymmetric calix[4]arene, there are four possible regioisomeric mono-O-alkyl derivatives, and for the partial cone conformation, four diastereomeric tetraderivatives are possible.
-
-
-
-
43
-
-
0027221103
-
-
S. Pickard, W. H. Pirkle, M. Tabatabai, W. Vogt, V. Böhmer, Chirality 1993, 5, 310-314.
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Chirality
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Pickard, S.1
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Tabatabai, M.3
Vogt, W.4
Böhmer, V.5
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44
-
-
33748818719
-
-
note
-
The presence of remaining phenolic OH groups seems to be important for the effective interaction with the stationary phase.
-
-
-
-
45
-
-
0012009659
-
-
1-relaxation measurements: e.g. A. Yamada, T. Murase, K. Kikukawa, T. Arimura, S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1991, 793-797.
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(1991)
J. Chem. Soc., Perkin Trans. 2
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Yamada, A.1
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Kikukawa, K.3
Arimura, T.4
Shinkai, S.5
-
46
-
-
0006103265
-
-
For tungsten derivatives of calix[4]arenes see: L. Giannini, E. Solari, A. Zanotti-Gerosa, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Angew. Chem. 1996, 108, 3051-3053, and references cited therein.
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Angew. Chem.
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Giannini, L.1
Solari, E.2
Zanotti-Gerosa, A.3
Floriani, C.4
Chiesi-Villa, A.5
Rizzoli, C.6
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47
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0006095602
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B. Xu, P. J. Carroll, T. M. Swager, Angew. Chem. 1996, 108, 2238-2242.
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Angew. Chem.
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Xu, B.1
Carroll, P.J.2
Swager, T.M.3
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48
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84972804530
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M. Tabatabai, W. Vogt, V. Böhmer, G. Ferguson, E. F. Paulus, Supramol. Chem. 1995, 4, 147-152.
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Supramol. Chem.
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Tabatabai, M.1
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Ferguson, G.4
Paulus, E.F.5
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49
-
-
33748810678
-
-
note
-
4/dioxane method was initially developed for the synthesis of these bridged calix[4]arenes.
-
-
-
-
50
-
-
37049110520
-
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V. Böhmer, H. Goldmann, W. Vogt, J. Chem. Soc., Chem. Commun. 1985, 667-668.
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(1985)
J. Chem. Soc., Chem. Commun.
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Böhmer, V.1
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51
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33845278966
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H. Goldmann, W. Vogt, E. Paulus, V. Böhmer, J. Am. Chem. Soc. 1988, 110, 6811-6817.
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J. Am. Chem. Soc.
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Goldmann, H.1
Vogt, W.2
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Böhmer, V.4
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52
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0029004184
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2 bridge see: A. Arduini, S. Fanni, A. Pochini, A. R. Sicuri, R. Ungaro, Tetrahedron, 1995, 51, 7951-7958;
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(1995)
Tetrahedron
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Arduini, A.1
Fanni, S.2
Pochini, A.3
Sicuri, A.R.4
Ungaro, R.5
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53
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0002038377
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2 bridge see: O. Struck, J. P. M. van Duynhoven, W. Verboom, S. Harkema, D. N. Reinhoudt, J. Chem. Soc., Chem. Commun. 1996, 1517-1518
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(1996)
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Struck, O.1
Van Duynhoven, J.P.M.2
Verboom, W.3
Harkema, S.4
Reinhoudt, D.N.5
-
54
-
-
33748817947
-
-
private communication
-
Even with a single methylene group as the bridge a (necessarily totally distorted) cone conformation is found in the crystalline state (D. N. Reinhoudt et al., private communication).
-
-
-
Reinhoudt, D.N.1
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55
-
-
37049075647
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E. Paulus, V. Böhmer, H. Goldmann, W. Vogt, J. Chem. Soc., Perkin Trans. 2, 1987, 1609-1615.
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(1987)
J. Chem. Soc., Perkin Trans. 2
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Paulus, E.1
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Vogt, W.4
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56
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37049084266
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V. Böhmer, H. Goldmann, W. Vogt, E. F. Paulus, F. L. Tobiason, M. J. Thielman, J. Chem. Soc., Perkin Trans. 2, 1990, 1769-1775.
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J. Chem. Soc., Perkin Trans. 2
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Böhmer, V.1
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0005692995
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V. Böhmer, H. Goldmann, R. Kaptein, L. Zetta, J. Chem. Soc., Chem. Commun. 1987, 1358-1360.
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J. Chem. Soc., Chem. Commun.
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Böhmer, V.1
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0001635626
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R. M. Izatt, J. D. Lamb, R. T. Hawkins, P. R. Brown, S. R. Izatt, J. J. Christensen, J. Am. Chem. Soc. 1983, 105, 1782;
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Izatt, R.M.1
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59
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33845379405
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S. R. Izatt, R. T. Hawkins, J. J. Christansen, R. M. Izatt, J. Am. Chem. Soc. 1985, 107, 63-65.
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Izatt, S.R.1
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60
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37049077745
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R. Assmus, V. Böhmer, J. M. Harrowfield, M. I. Ogden, W. R. Richmond, B. W. Skelton, A. H. White, J. Chem. Soc., Dalton Trans. 1993, 2427-2433.
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J. Chem. Soc., Dalton Trans.
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Assmus, R.1
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61
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84986959178
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F. Arnaud-Neu, V. Böhmer, L. Guerra, M. A. McKervey, E. F. Paulus, A. Rodriguez, M.-J. Schwing-Weill, M. Tabatabai, W. Vogt, J. Phys. Org. Chem. 1992, 5, 471-481.
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Arnaud-Neu, F.1
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2 group is impossible in the tetraanion of 19a which is formed most probably under alkaline conditions by deprotonation of the OH-groups.
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E. F. Paulus, M. Frings, A. Shivanyuk, V. Böhmer, W. Vogt, unpublished.
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[86].
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