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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
Authors:Yuan‐Yin Chen  Yi‐Kun Chen  Shu‐Ling Gong  Zu‐Nong Gao
Abstract:With a variation in reaction conditions, 1, 4‐bis (2‐(2‐chloroethoxy)ethoxy)‐calix6]arene (3) and l,3,5‐tris(2‐(2‐chloroethoxy) ethoxy)‐calix 6] arene (4) or 4 and 4‐chloroethoxyethoxy‐calix6]crown‐3 (5) were selectively synthesized from p‐tert‐butyl‐calix 6] arene and 2‐(2‐chloroethoxy)ethyltosylate. l,3–4,6‐p‐tert‐butylcalix6]‐bis‐crown‐3 (6) with (u,u,u,d,d,d) conformation and 1,3–4,5‐p‐tert‐butylcalix6]‐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‐calix6]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.
Keywords:Calix[6]arene  crown ether  calixcrown  synthesis
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