On the Conformational Isomers in Tetra-O-alkylcalix[4]arenes

作者: Koji Araki , Koji Iwamoto , Seiji Shinkai , Tsutomu Matsuda

DOI: 10.1246/CL.1989.1747

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摘要: p-t-Butylcalix[4]arene (14H) was alkylated with RX (R = Me, Et, Pr, and Bu) the products (14R) were analyzed by HPLC 1H NMR. It found that (i) ring inversion arising from oxygen-through-the-annulus rotation can be inhibited R greater than (ii) “cone” “partial cone” result in a 1:1 ratio, (iii) thermodynamically, conformation is most stable.

参考文章(8)
C.David Gutsche, Balram Dhawan, Jeffrey A. Levine, Kwang Hyun No, Lorenz J. Bauer, Calixarenes 9 : Conformational isomers of the ethers and esters of calix[4]arenes Tetrahedron. ,vol. 39, pp. 409- 426 ,(1983) , 10.1016/S0040-4020(01)88541-0
C. D. Gutsche, M. Iqbal, K. S. Nam, K. See, I. Alam, Conformational and complexational characteristics of calixarenes Pure and Applied Chemistry. ,vol. 60, pp. 483- 488 ,(1988) , 10.1351/PAC198860040483
C. David Gutsche, Lorenz J. Bauer, Calixarenes. 14. The conformational properties of the ethers and esters of the calix[6]arenes and the calix[8]arenes Journal of the American Chemical Society. ,vol. 107, pp. 6059- 6063 ,(1985) , 10.1021/JA00307A039
Volker Boehmer, Frank Marschollek, Lucia Zetta, Calix[4]arenes with four differently substituted phenolic units Journal of Organic Chemistry. ,vol. 52, pp. 3200- 3205 ,(1987) , 10.1021/JO00391A005
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
Takashi Arimura, Seiji Shinkai, Tsutomu Matsuda, Yoshimi Hirata, Hiroshi Satoh, Osamu Manabe, Fries Rearrangement in Calixarene Esters: A New Entry for the Synthesis of p-Substituted Calixarenes Bulletin of the Chemical Society of Japan. ,vol. 61, pp. 3733- 3734 ,(1988) , 10.1246/BCSJ.61.3733
Arturo Arduini, Andrea Pochini, Sara Reverberi, Rocco Ungaro, Giovanni D. Anreetti, Franco Ugozzoli, The preparation and properties of a new lipophilic sodium selective ether ester ligand derived from p-t-butylcalix[4]arene Tetrahedron. ,vol. 42, pp. 2089- 2100 ,(1986) , 10.1016/S0040-4020(01)87626-2
H. Casablanca, J. Royer, A. Satrallah, A. Taty-C, J. Vicens, Synthesis of calix[4]arenes presenting no plane of symmetry Tetrahedron Letters. ,vol. 28, pp. 6595- 6596 ,(1987) , 10.1016/S0040-4039(00)96922-3