Singly bridged calix[8]crowns

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5143-5151

  Geraci, Corrada ^b   Piattelli, Mario ^b   Chessari, Gianni ^b   Neri, Placido ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CROWN ETHER DERIVATIVE; POLYETHER DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; ISOMER; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034714408     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0002036     Document Type: Article

References (71)

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37. (a) Under similar conditions NaH promoted the 1,4-bridging of p-tert-butylcalix[8]arene with some bis(bromomethyl)arene derivatives: Ikeda, A.; Akao, K.; Harada, T.; Shinkai, S. Tetrahedron Lett. 1996, 37, 1621.
38. (b) The 1,4-bridging with an acridone-based linker was also reported: Tsantrizos, Y. S.; Chew, W.; Colebrook, L. D.; Sauriol, F. Tetrahedron Lett. 1997, 38, 5411.
39. The general principle of this approach has been detailed in ref 10 and in: Neri, P.; Consoli, G. M. L.; Cunsolo, F.; Geraci, C.; Piattelli, M. New J. Chem. 1996, 20, 443.
40. The validity of this "downfield displacement" rule and the comparison of OH chemical shift in a series of partial methoxycalix[8]arenes have been discussed in: Cunsolo, F.; Consoli, G. M. L.; Piattelli, M.; Neri, P. J. Org. Chem. 1998, 63, 6852.
41. For other examples of the use of OH chemical shift as a structural probe, see refs 8a, 16, and: Neri, P.; Battocolo, E.; Cunsolo, F.; Geraci, C.; Piattelli, M. J. Org. Chem. 1994, 59, 3880.
42. Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161. Keller, S. W.; Schuster, G. M.; Tobiason, F. L. Polym. Mater. Sci. Eng. 1987, 57, 906. The OH chemical shift in "large" calix[n]arenes (n = 9-20) has been comparatively discussed in: Stewart, D. R.; Gutsche, C. D. J. Am. Chem. Soc. 1999, 121, 4136.
43. Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161. Keller, S. W.; Schuster, G. M.; Tobiason, F. L. Polym. Mater. Sci. Eng. 1987, 57, 906. The OH chemical shift in "large" calix[n]arenes (n = 9-20) has been comparatively discussed in: Stewart, D. R.; Gutsche, C. D. J. Am. Chem. Soc. 1999, 121, 4136.
44. Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161. Keller, S. W.; Schuster, G. M.; Tobiason, F. L. Polym. Mater. Sci. Eng. 1987, 57, 906. The OH chemical shift in "large" calix[n]arenes (n = 9-20) has been comparatively discussed in: Stewart, D. R.; Gutsche, C. D. J. Am. Chem. Soc. 1999, 121, 4136.
45. For a discussion on the OH chemical shift in partial alkoxycalix[4]arenes, see: Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 1990, 63, 3480. Groenen, L.; Steinwender, E.; Lutz, B.; van der Maas, J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1992, 1893. Similarly, for the partial alkoxycalix[6]arene series, see: Otsuka, H.; Araki, K.; Shinkai, S. J. Org. Chem. 1994, 59, 1542. Janssen, R. G.; Verboom, W.; Lutz, B. G.; van der Maas, J. H.; Maczka, M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1996, 1869.
46. For a discussion on the OH chemical shift in partial alkoxycalix[4]arenes, see: Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 1990, 63, 3480. Groenen, L.; Steinwender, E.; Lutz, B.; van der Maas, J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1992, 1893. Similarly, for the partial alkoxycalix[6]arene series, see: Otsuka, H.; Araki, K.; Shinkai, S. J. Org. Chem. 1994, 59, 1542. Janssen, R. G.; Verboom, W.; Lutz, B. G.; van der Maas, J. H.; Maczka, M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1996, 1869.
47. For a discussion on the OH chemical shift in partial alkoxycalix[4]arenes, see: Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 1990, 63, 3480. Groenen, L.; Steinwender, E.; Lutz, B.; van der Maas, J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1992, 1893. Similarly, for the partial alkoxycalix[6]arene series, see: Otsuka, H.; Araki, K.; Shinkai, S. J. Org. Chem. 1994, 59, 1542. Janssen, R. G.; Verboom, W.; Lutz, B. G.; van der Maas, J. H.; Maczka, M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1996, 1869.
48. For a discussion on the OH chemical shift in partial alkoxycalix[4]arenes, see: Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 1990, 63, 3480. Groenen, L.; Steinwender, E.; Lutz, B.; van der Maas, J.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1992, 1893. Similarly, for the partial alkoxycalix[6]arene series, see: Otsuka, H.; Araki, K.; Shinkai, S. J. Org. Chem. 1994, 59, 1542. Janssen, R. G.; Verboom, W.; Lutz, B. G.; van der Maas, J. H.; Maczka, M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Chem. Soc., Perkin Trans. 2 1996, 1869.
49. Rogers, J. S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3152. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3160.
50. Rogers, J. S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3152. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3160.
51. For a discussion on the behavior of a preformed calix[8]arene trianion, see: Neri, P.; Consoli, G. M. L.; Cunsolo, F.; Rocco, C.; Piattelli, M. J. Org. Chem. 1997, 62, 4236.
52. This template effect has also been invoked to explain the formation of 1,2-calix[4]crown: Yamamoto, H.; Sakaki, T.; Shinkai, S. Chem. Lett. 1994, 469.
53. Neri, P.; Geraci, C.; Piattelli, M. J. Org. Chem. 1995, 60, 4126. Consoli, G. M. L.; Cunsolo, F., Neri, P. Gazz. Chim. Ital. 1996, 126, 791.
54. Neri, P.; Geraci, C.; Piattelli, M. J. Org. Chem. 1995, 60, 4126. Consoli, G. M. L.; Cunsolo, F., Neri, P. Gazz. Chim. Ital. 1996, 126, 791.
55. Dijkstra, G.; Hruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230. Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325. Shinkai, S. Tetrahedron 1993, 49, 8933 and references therein.
56. Dijkstra, G.; Hruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230. Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325. Shinkai, S. Tetrahedron 1993, 49, 8933 and references therein.
57. Dijkstra, G.; Hruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230. Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325. Shinkai, S. Tetrahedron 1993, 49, 8933 and references therein.
58. Clague, N. P.; Clegg, W.; Coles, S. J.; Crane, J. D.; Moreton, D. J.; Sinn, E.; Teat S. J.; Young, N. A. Chem. Commun. 1999, 379. This conformation was first suggested by Gutsche: Gutsche, C. D.; Bauer, L. J. Tetrahedron Lett. 1981, 22, 4763.
59. Clague, N. P.; Clegg, W.; Coles, S. J.; Crane, J. D.; Moreton, D. J.; Sinn, E.; Teat S. J.; Young, N. A. Chem. Commun. 1999, 379. This conformation was first suggested by Gutsche: Gutsche, C. D.; Bauer, L. J. Tetrahedron Lett. 1981, 22, 4763.
60. Czugler, M.; Tisza, S.; Speier, G. J. Incl. Phenom. Mol. Recognit. Chem. 1991, 11, 323.
61. 14a
62. For a discussion on the conformational restriction by the residual hydrogen bonding in mono-O-substituted calix[6]arenes, see: Magrans, J. O.; Rincon, A. M.; Cuevas, F.; Lopez-Prados, J.; Nieto, P. M.; Pons, M.; Prados, P.; de Mendoza, J. J. Org. Chem. 1998, 63, 1079.
63. It is worth to recall here that the tert-butyl through the annulus passage in unbridged p-tert-butylcalix[8]arenes is always operating as demonstrated by the fact that it occurs even in the smaller p-tert-butylcalix[6]arenes: Otsuka, H.; Araki, K.; Sakaki, T.; Nakashima, K.; Shinkai, S. Tetrahedron Lett. 1993, 34, 7275. van Duynhoven, J. P. M.; Janssen, R. G.; Verboom, W.; Franken, S. M.; Casnati, A.; Pochini, A.; Ungaro, R.; de Mendoza, J.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 5814. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1994, 59, 3871.
64. It is worth to recall here that the tert-butyl through the annulus passage in unbridged p-tert-butylcalix[8]arenes is always operating as demonstrated by the fact that it occurs even in the smaller p-tert-butylcalix[6]arenes: Otsuka, H.; Araki, K.; Sakaki, T.; Nakashima, K.; Shinkai, S. Tetrahedron Lett. 1993, 34, 7275. van Duynhoven, J. P. M.; Janssen, R. G.; Verboom, W.; Franken, S. M.; Casnati, A.; Pochini, A.; Ungaro, R.; de Mendoza, J.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 5814. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1994, 59, 3871.
65. It is worth to recall here that the tert-butyl through the annulus passage in unbridged p-tert-butylcalix[8]arenes is always operating as demonstrated by the fact that it occurs even in the smaller p-tert-butylcalix[6]arenes: Otsuka, H.; Araki, K.; Sakaki, T.; Nakashima, K.; Shinkai, S. Tetrahedron Lett. 1993, 34, 7275. van Duynhoven, J. P. M.; Janssen, R. G.; Verboom, W.; Franken, S. M.; Casnati, A.; Pochini, A.; Ungaro, R.; de Mendoza, J.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 5814. Kanamathareddy, S.; Gutsche, C. D. J. Org. Chem. 1994, 59, 3871.
66. Molecular modeling was performed with the MacroModel V4.5 computer program: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
67. On the basis of computer models this conclusions should also be applicable to the corresponding 1,5-crown-4 derivative. However, in this case the difficulty encountered in obtaining a sufficiently pure compound impeded the experimental NMR confirmation.
68. Arduini, A.; Pochini, A.; Reverberi, S.; Ungaro, R.; Andreetti, G. D.; Ugozzoli, F. Tetrahedron 1986, 42, 2089.
69. Ikeda, A.; Suzuki, Y.; Shinkai, S. Tetrahedron: Asymmetry 1998, 9, 97. Geraci, C.; Bottino, A.; Piattelli, M.; Gavuzzo, E.; Neri, P. J. Chem. Soc., Perkin Trans. 2 2000, 185.
70. Ikeda, A.; Suzuki, Y.; Shinkai, S. Tetrahedron: Asymmetry 1998, 9, 97. Geraci, C.; Bottino, A.; Piattelli, M.; Gavuzzo, E.; Neri, P. J. Chem. Soc., Perkin Trans. 2 2000, 185.
71. Munch, J. H.; Gutsche, C. D. Org. Synth. 1989, 68, 243.