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Selective Preparation of Isomeric Tetrahydroxypillar[5]arenes and Pillar[3]arene[2]quinones
Author(s) -
Pan Mingguang,
Xue Min
Publication year - 2013
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.201300455
Subject(s) - chemistry , pillar , yield (engineering) , quinone , salt (chemistry) , medicinal chemistry , calixarene , stereochemistry , organic chemistry , molecule , structural engineering , engineering , materials science , metallurgy
The isomeric tetrahydroxylated pillar[5]arenes were synthesized through partial oxidation of 1,4‐dimethoxypillar[5]arene or 1,4‐dimethoxypillar[4]arene[1]quinone by (NH 4 ) 2 [Ce(NO 3 ) 6 ] and then reduction by Na 2 S 2 O 4 . The intermediate 1,4‐dimethoxypillar[3]arene[2]quinones have two constitutional isomers. The yield of the 1,3‐isomer 1 can reach 42 %, and was far higher than that of the 1,2‐isomer 2 (formed in trace amounts). The approach provides an efficient way to prepare constitutional‐isomeric selectively functionalized pillar[5]arenes 3 and 4 . Furthermore, the host–guest complexation of 3 and 4 with a bis(imidazolium) salt was investigated.