The high yielding synthesis of pillar[5]arenes under Friedel-Crafts conditions explained by dynamic covalent bond formation.

Systematic investigations of the cyclooligomerization of 1,4-disubstituted hydroquinone derivatives under Friedel-Crafts conditions have been carried out to demonstrate that the formation of pillar[5]arenes occurs under thermodynamic control.

[1]  K. Sharma,et al.  Pillar[5]arenes: fascinating cyclophanes with a bright future. , 2012, Chemical Society reviews.

[2]  Feihe Huang,et al.  Preparation of Pillar[n]arenes by Cyclooligomerization of 2,5‐Dialkoxybenzyl Alcohols or 2,5‐Dialkoxybenzyl Bromides , 2011 .

[3]  William R. Dichtel,et al.  A mechanistic study of Lewis acid-catalyzed covalent organic framework formation , 2011 .

[4]  Zhenxia Chen,et al.  Self-assembly and proton conductance of organic nanotubes from pillar[5]arenes , 2011 .

[5]  Y. Yu,et al.  Pillar[5]arene decaamine: synthesis, encapsulation of very long linear diacids and formation of ion pair-stopped [2]rotaxanes. , 2011, Chemical communications.

[6]  J. F. Stoddart,et al.  Monofunctionalized pillar[5]arene as a host for alkanediamines. , 2011, Journal of the American Chemical Society.

[7]  C. Price.  The Alkylation of Aromatic Compounds by the Friedel‐Crafts Method , 2011 .

[8]  Feihe Huang,et al.  Four constitutional isomers of BMpillar[5]arene: synthesis, crystal structures and complexation with n-octyltrimethyl ammonium hexafluorophosphate. , 2011, Chemical communications.

[9]  T. Ogoshi,et al.  Planar-chiral pillar[5]arene: chiral switches induced by multiexternal stimulus of temperature, solvents, and addition of achiral guest molecule. , 2011, The Journal of organic chemistry.

[10]  S. Fujinami,et al.  Facile, rapid, and high-yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure. , 2011, The Journal of organic chemistry.

[11]  Y. Yu,et al.  Self-assembly of [2]pseudorotaxanes based on pillar[5]arene and bis(imidazolium) cations. , 2010, Chemical communications.

[12]  D. Schollmeyer,et al.  Synthesis and Conformational Properties of Nonsymmetric Pillar[5]arenes and Their Acetonitrile Inclusion Compounds , 2010 .

[13]  T. Ogoshi,et al.  High Yield Synthesis of Polyrotaxane Constructed from Pillar[5]arene and Viologen Polymer and Stabilization of Its Radical Cation , 2010 .

[14]  M. Mastalerz.  Shape-persistent organic cage compounds by dynamic covalent bond formation. , 2010, Angewandte Chemie.

[15]  Feihe Huang,et al.  Syntheses of copillar[5]arenes by co-oligomerization of different monomers. , 2010, Organic letters.

[16]  T. Ogoshi,et al.  Synthesis, conformational and host-guest properties of water-soluble pillar[5]arene. , 2010, Chemical communications.

[17]  Chunju Li,et al.  Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives. , 2010, Organic & biomolecular chemistry.

[18]  T. Ogoshi,et al.  Synthesis and conformational characteristics of nonsymmetric pillar[5]arene. , 2010, Organic letters.

[19]  Lingyun Wang,et al.  A facile and efficient preparation of pillararenes and a pillarquinone. , 2009, Angewandte Chemie.

[20]  T. Ogoshi,et al.  Through-space pi-delocalized Pillar[5]arene. , 2009, Chemical communications.

[21]  M. Zeng,et al.  Chiral Brønsted acid catalyzed Friedel-Crafts alkylation reactions. , 2009, Chemical Society reviews.

[22]  K. Jørgensen,et al.  Catalytic asymmetric Friedel-Crafts alkylation reactions--copper showed the way. , 2008, Chemical reviews.

[23]  Yoshiaki Nakamoto,et al.  para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. , 2008, Journal of the American Chemical Society.

[24]  R. Maggi,et al.  Use of solid catalysts in Friedel-Crafts acylation reactions. , 2006, Chemical reviews.

[25]  Stuart J Rowan,et al.  Dynamic covalent chemistry. , 2002, Angewandte Chemie.

[26]  Jean-Marie Lehn,et al.  Dynamic Combinatorial Chemistry and Virtual Combinatorial Libraries , 1999 .

[27]  Gutsche Cd,et al.  Pathways for the Reversion of p-tert-Butylcalix[8]arene top-tert-Butylcalix[4]arene(1). , 1999 .

[28]  N. O. Calloway.  The Friedel-Crafts Syntheses. , 1935 .