Synthesis of p-tert-Butyl-calix[6] -biscrown-3 via Intramolecular Ring-closure of 1,4-Bis (2-(2-chloroethoxy) ethoxy) -p-tert-butyl-calix[6]arene

✍ Scribed by Yuan-Yin Chen; Yi-Kun Chen; Shu-Ling Gong; Zu-Nong Gao

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 355 KB
• Volume: 19
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.20010190318

✦ Synopsis

Abstract

With a variation in reaction conditions, 1, 4‐bis (2‐(2‐chloroethoxy)ethoxy)‐calix[6]arene (3) and l,3,5‐tris(2‐(2‐chloroethoxy) ethoxy)‐calix [6] arene (4) or 4 and 4‐chloroethoxyethoxy‐calix[6]crown‐3 (5) were selectively synthesized from p‐tert‐butyl‐calix [6] arene and 2‐(2‐chloroethoxy)ethyltosylate. l,3–4,6‐p‐tert‐butylcalix[6]‐bis‐crown‐3 (6) with (u,u,u,d,d,d) conformation and 1,3–4,5‐p‐tert‐butylcalix[6]‐biscrown‐3 (7) with self‐anchored (u,u, u, u, u, d) conformation were synthesized through an intramolecularly ring‐closing condensation of 1, 4‐bis (2‐(2‐chloroethoxy)ethoxy)‐p‐tert‐butyl‐calix[6]arene (3) in 25% and 15% yield, respectively. Using 5 instead of 3, only 7 was obtained in 65% high yield. 6 and 7 show different complexation properties toward alkali metal and ammonium ions.