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Remarkable Stability of Imino Macrocycles in Water
Author(s) -
Saggiomo Vittorio,
Lüning Ulrich
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800462
Subject(s) - diimine , chemistry , methanol , yield (engineering) , polymer chemistry , ion , calcium , combinatorial chemistry , organic chemistry , catalysis , metallurgy , materials science
Imines 3 , 5 and 7 generated from 4‐methoxypyridine‐2,6‐dicarbaldehyde ( 1 ) and several amines 2 , 4 and 6 show a remarkable stability in water. The 18‐membered macrocyclic diimine 5 is stable and could be synthesized in good yield by using 2 equiv. of calcium ions as template in pure water, and even the non‐macrocyclic diimine 3 survives in water/methanol (50:50) without any template effect. In a mixture of pyridinedicarbaldehyde 1 and two glycol‐derived diamines 4 and 6 , a calcium template ion selects the 18‐membered macrocycle 5 over the 20‐membered one ( 7 ). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)