Preparation of Pillar[n]arenes by Cyclooligomerization of 2,5-Dialkoxybenzyl Alcohols or 2,5-Dialkoxybenzyl Bromides

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 27; pp. 5331 - 5335
• Main Authors: Ma, Yingjie, Zhang, Zibin, Ji, Xiaofan, Han, Chengyou, He, Jiuming, Abliz, Zeper, Chen, Weixiang, Huang, Feihe
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Arenes; Calixarenes; Chemistry; Chemistry, Organic; Cross-disciplinary physics: materials science; rheology; Cyclooligomeri­zation; Exact sciences and technology; Host-guest systems; Macrocycles; Materials science; Methods of nanofabrication; Organic chemistry; Physical Sciences; Physics; Pillar[n]arenes; Preparations and properties; Science & Technology; Supramolecular and biochemical assembly; Supramolecular chemistry; CRYPTAND/PARAQUAT; Calixarenes; Arenes; Pillar[n]arenes; HOST; Macrocycles; FACILE; Supramolecular chemistry; Host-guest systems; Cyclooligomerization; HIGH-YIELD SYNTHESIS; Arene; Organic bromine compounds; Calixarene; Host―guest systems; Alcohols; Macrocycle; Aromatics; Inclusion compounds; Supramolecular structure; Cyclophane; Chemical synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201100698

The facile and efficient preparation of pillar[n]arenes (n = 5 or 6) was achieved by cyclooligomerization of 2,5‐dialkoxybenzyl alcohols or 2,5‐dialkoxybenzyl bromides with an appropriate Lewis acid catalyst at room temperature. The mechanism for this cyclooligomerization is presumed to be a Friedel–Crafts alkylation. The facile and efficient preparation of pillar[n]arenes (n = 5 or 6) was achieved by cyclooligomerization of 2,5‐dialkoxybenzyl alcohols or 2,5‐dialkoxybenzyl bromideswith an appropriate Lewis acid catalyst at room temperature. The mechanism for this cyclooligomerization is presumed to be a Friedel–Crafts alkylation.