Unprecedented cyclizations of calix[4]arenes with glycols under the Mitsunobu protocol, part 2.(1) O,O-and O,S-bridged calixarenes

Viktor Csokai; Alajos Grün; Barbara Balázs; Gábor Tóth; Gyula Horváth; István Bitter

doi:10.1021/ol0359315

Unprecedented cyclizations of calix[4]arenes with glycols under the Mitsunobu protocol, part 2.(1) O,O-and O,S-bridged calixarenes

Org Lett. 2004 Feb 19;6(4):477-80. doi: 10.1021/ol0359315.

Authors

Viktor Csokai¹, Alajos Grün, Barbara Balázs, Gábor Tóth, Gyula Horváth, István Bitter

Affiliation

¹ Budapest University of Technology and Economics, H-1521 Budapest, Hungary, and IVAX Drug Research Institute, Ltd., H-1325 Budapest, Hungary.

PMID: 14961602
DOI: 10.1021/ol0359315

Abstract

[reaction: see text] Cycloalkylations of p-tert-butylcalix[4]arene (CA) and p-tert-butylthiacalix[4]arene (TCA) with various aliphatic glycols were performed under the Mitsunobu protocol using the DEAD/TPP system. CA gave 1,3-dialkylated diols, while C(2)-C(10) glycols gave 1,2- and 1,3-bridged calixarenes. The reaction of TCA with C(2) diols afforded sulfonium phenoxide betaines via O,S-cyclization, which is the first example for the alkylation of the sulfide bridge.