A "classical" tetrahydroxycalix[4]arene adopting the 1,2-alternate conformation.

作者: Samah Simaan , Silvio E. Biali

DOI: 10.1021/JO035573J

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摘要: The first example of a “classical” tetrahydroxycalixarene, which adopts the 1,2-alternate conformation both in solution and crystal, is described. Calixarene derivatives with two distal methylene groups substituted trans fashion by phenyl (5a) or mesityl (5b) were synthesized via addition PhMgBr/CuCN MesMgBr/CuCN to bis(spirodiene) derivative 3. Whereas phenyl-substituted calixarene 5a usual “cone” conformation, NMR data X-ray crystallography indicate that more crowded 5b located at isoclinal positions macrocycle.

参考文章(14)
Seiji Shinkai, Takeshi Nagasaki, Koji Iwamoto, Atsushi Ikeda, G.-X. He, Tsutomu Matsuda, Masakazu Iwamoto, New syntheses and physical properties of p-alkylcalix(n)arenes. Bulletin of the Chemical Society of Japan. ,vol. 64, pp. 381- 386 ,(1991) , 10.1246/BCSJ.64.381
Cordula Grüttner, Volker Böhmer, Walter Vogt, Iris Thondorf, Silvio E. Biali, Flavio Grynszpan, Calix[4]arenes with alkylidene bridges, synthesis and conformational properties Tetrahedron Letters. ,vol. 35, pp. 6267- 6270 ,(1994) , 10.1016/S0040-4039(00)73408-3
Oren Golan, Lutz Fitjer, Silvio E. Biali, Jörg Weiser, Chair/Twist-Boat Energy Gap in Monocyclic, Conformationally Unconstrained Polyalkylcyclohexanes. Journal of Organic Chemistry. ,vol. 61, pp. 8277- 8284 ,(1996) , 10.1021/JO961526Y
Cédric Desroches, Stéphane Parola, Francis Vocanson, Monique Perrin, Roger Lamartine, Jean-Marie Létoffé, Jean Bouix, Nitration of thiacalix[4]arene using nitrosium nitrate complexes: synthesis and characterization of tetranitro-, tetraamino-, and tetra(4-pyridylimino)tetrahydroxythiacalix[4]arene New Journal of Chemistry. ,vol. 26, pp. 651- 655 ,(2002) , 10.1039/B110609K
Noa Seri, Samah Simaan, Mark Botoshansky, Menahem Kaftory, Silvio E. Biali, A conformationally flexible tetrahydroxycalix[4]arene adopting the unusual 1,3-alternate conformation Journal of Organic Chemistry. ,vol. 68, pp. 7140- 7142 ,(2003) , 10.1021/JO034874Q
C. David Gutsche, Lorenz J. Bauer, Calixarenes. 13. The conformational properties of calix[4]arenes, calix[6]arenes, calix[8]arenes, and oxacalixarenes Journal of the American Chemical Society. ,vol. 107, pp. 6052- 6059 ,(1985) , 10.1021/JA00307A038
Kasim Agbaria, Silvio E. Biali, Spirodienone route for the stereoselective methylene functionalization of p-tert-butylcalix[4]arene. Journal of the American Chemical Society. ,vol. 123, pp. 12495- 12503 ,(2001) , 10.1021/JA0117480