Synthesis of calix[6]arenes partially functionalized at the upper rim


Casnati, Alessandro and Domiano, Laura and Pochini, Andrea and Ungaro, Rocco and Carramolino, Mar and Magrans, J. Oriol and Nieto, Pedro M. and Lopez-Prados, Javier and Prados, Pilar and Mendoza, Javier de and Janssen, Rob G. and Verboom, Willem and Reinhoudt, David N. (1995) Synthesis of calix[6]arenes partially functionalized at the upper rim. Tetrahedron, 51 (46). pp. 12699-12720. ISSN 0040-4020

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Abstract:Several new examples of calix[6]arenes selectively functionalized at the upper rim are reported. Starting from calix[6]arenes 1,3,5-tri-, 1,2,4,5-tetra- and 1,2,3,4,5-pentaalkylated at the lower rim, it is possible to isolate macrocycles 2,4,6-tri-, 3,6-di- and 6-mono functionalized at the upper rim (18¿94% yield) with nitro, formyl, bromo, chloromethyl and 2-propenyl groups. Modifications of these moieties allow the synthesis of macrocycles bearing amino, amido, hydroxymethyl, carboxy, cyano and chloromethyl functions which can be used for further transformation and preparation of new molecular receptors, based on calix[6]arenes, which have different geometries. Examples of di- and triquinones on the hexameric macrocycle are also reported.
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Copyright:© 1995 Elsevier Science
Science and Technology (TNW)
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Metis ID: 106642