The formylation of the upper-rims of thiacalixarenes: synthesis of the first tetra-formylated and the first meta-substituted thiacalix[4]arenes

Abstract

The conventional Gross reaction for the formylation of the tetrapropoxythiacalix[4]arene using TiCl4 affords the 18-(chloromethyl)-28-hydroxy-25,26,27-tripropoxythiacalix[4]arene substituted in the meta-position of the macrocycle. The p-tetraformyl-tetrapropoxythiacalix[4]arene, which is an interesting intermediate to the upper-rims functionalization of thiacalixarenes, was prepared with a very good yield using BuLi and N-formylpiperidine. (C) 2004 Published by Elsevier Ltd.

Keywords

calixarene; formylation; chloromethylation; meta-substitution

Published in

Tetrahedron Letters
2004, volume: 45, number: 33, pages: 6329-6331
Publisher: PERGAMON-ELSEVIER SCIENCE LTD

SLU Authors

• Kessler, Vadim

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

Publication identifier

• DOI: https://doi.org/10.1016/j.tetlet.2004.06.078

Permanent link to this page (URI)

https://res.slu.se/id/publ/2915