Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes

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Groenen, Leo C. and Ruel, Bianca H.M. and Casnati, Alessandro and Timmerman, Peter and Verboom, Willem and Harkema, Sybolt and Pochini, Andrea and Ungaro, Rocco and Reinhoudt, David N. (1991) Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes. Tetrahedron Letters, 32 (23). pp. 2675-2678. ISSN 0040-4039

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Abstract:In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 4-6 can be isolated in 15-55 % from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.
Item Type:Article
Copyright:© 1991 Elsevier Science
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/12508
Official URL:http://dx.doi.org/10.1016/S0040-4039(00)78816-2
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