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

Autor: Groenen, L.C., Groenen, Leo C., Ruel, Bianca H.M., Casnati, Alessandro, Timmerman, P., Verboom, Willem, Harkema, Sybolt, Pochini, Andrea, Ungaro, Rocco, Reinhoudt, David
Přispěvatelé: Faculty of Science and Technology, Molecular Nanofabrication
Rok vydání: 1991
Předmět:
Zdroj: Tetrahedron letters, 0(32), 2675-2678. Elsevier
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)78816-2
Popis: 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.
Databáze: OpenAIRE