Calix[4]arenes bearing α-amino- or α-hydroxyphosphonic acid fragments at the upper rim

✍ Scribed by Andrew Solovyov; Sergey Cherenok; Ivan Tsymbal; Salvatore Failla; Giuseppe A. Consiglio; Paolo Finocchiaro; Vitaly Kalchenko

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 208 KB
• Volume: 12
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.2

✦ Synopsis

Abstract

By the reaction of para‐formylcalix[4]arenes 1–6 with trialkyl phosphites in the presence of dry hydrogen chloride, calix[4]arenes 7–13 possessing dialkylphosphoryl‐hydroxymethyl groupings at the upper rim were synthesized. Calix[4]arenes 18–23 functionalized with dialkylphosphoryl‐alkyl(aryl)aminomethyl groups were obtained by sodium‐promoted addition of dialkyl phosphites to C=N bonds of para‐iminocalix[4]arenes 14–17.

The consecutive treatment of α‐hydroxy‐ or α‐aminophosphonic acid dialkyl esters of calix[4]arenes 7, 10, 18, and 21 with bromotrimethylsilane and methanol gave dihydroxyphosphoryl derivatives of calix[4]arenes 24–27.

It was shown that calix[4]arenes bearing at the macrocyclic upper rim hydroxymethylphosphonic fragments, as well as bis‐hydroxymethyl(aminomethyl)phosphonic fragments, are able to undergo self‐assembly with formation of dimeric OH···O=P hydrogen bonded associates. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:58–67, 2001