Abstract
Hybrid [n]arenes, the class of medium-sized macrocyclic compounds consisting of different alkoxybenzene units, were obtained by a simple, one-pot, direct condensation of two different alkoxybenzenes with formaldehyde catalyzed by a Brønsted acid (trifluoroacetic acid). We have shown that, under Brønsted acid catalysis, this reaction is reversible and therefore governed by the relative stability of the products. The main macrocyclic products are hybrid [n]arenes consisting of four alkoxybenzene units of [2 + 2] or [3 + 1] stoichiometry. However, an unusual [3 + 2] hybrid macrocycle was also obtained as a main product of the condensation between 1,4-dimethoxybenzene, 1,3,5-trimethoxybenzene, and formaldehyde. The stability of the hybrid products and the reversibility of the reaction were further confirmed by a scrambling experiment, involving pillar[5]arene and per-O-methylated resorcin[4]arene. The scrambling experiment has given hybrid macrocycles in yields comparable with those obtained in condensation reactions. NMR spectra and X-ray structures of hybrid [n]arenes indicate that 1,2- and 1,3-dialkoxybenzene units are flexible parts of macrocyclic rings. However, the 1,4-dialkoxybenzene units present considerable steric hindran...Continue Reading
References
Dec 2, 2000·Organic Letters·M J McIldowieA H White
Mar 14, 2002·Chemistry : a European Journal·Jonathan L SesslerVladimír Král
Apr 12, 2002·Proceedings of the National Academy of Sciences of the United States of America·Jerry L AtwoodAgoston Jerga
May 11, 2002·Science·Jerry L AtwoodAgoston Jerga
Jul 18, 2002·Chemical Communications : Chem Comm·Magali DarzacJean-Pierre Dutasta
Aug 31, 2002·Chemistry : a European Journal·Grazia CafeoDavid J Williams
Jul 8, 2003·Analytical and Bioanalytical Chemistry·Chiara FrassinetiStefano Ghelli
Mar 25, 2005·Organic Letters·Arnaud GautierJean-Pierre Dutasta
Jul 30, 2005·The Journal of Organic Chemistry·Thierry BrotinJean-Pierre Dutasta
Jan 31, 2007·Organic Letters·Francesco TroisiPlacido Neri
Feb 22, 2007·Chemical Communications : Chem Comm·Sean P Bew, Sunil V Sharma
Mar 25, 2008·Journal of the American Chemical Society·Tomoki OgoshiYoshiaki Nakamoto
Aug 14, 2008·Journal of the American Chemical Society·Per Restorp, Julius Rebek
Mar 27, 2010·Organic & Biomolecular Chemistry·Chunju LiXueshun Jia
Jun 30, 2010·Organic Letters·Zibin ZhangFeihe Huang
Nov 9, 2010·Chemical Communications : Chem Comm·Chunju LiXueshun Jia
Feb 4, 2011·Angewandte Chemie·Zibin ZhangFeihe Huang
Mar 23, 2011·Chemical Communications : Chem Comm·Xiao-Bo HuJun-Li Hou
Mar 30, 2011·Journal of the American Chemical Society·Nathan L StruttJ Fraser Stoddart
Sep 15, 2011·Organic Letters·Orion B BerrymanJulius Rebek
Sep 29, 2011·Chemical Communications : Chem Comm·Huacheng ZhangJ Fraser Stoddart
Oct 19, 2011·The Journal of Organic Chemistry·Tomoki OgoshiTada-aki Yamagishi
Oct 19, 2011·Organic & Biomolecular Chemistry·Olusegun M FalanaRobert Stevenson
Nov 8, 2011·Angewandte Chemie·Wen SiZhan-Ting Li
Dec 14, 2011·Chemical Communications : Chem Comm·Michel HollerJean-François Nierengarten
Dec 22, 2011·Chemical Communications : Chem Comm·Nathan L StruttJ Fraser Stoddart
Feb 16, 2012·Journal of the American Chemical Society·Zhan ZhangJonathan L Sessler
Mar 1, 2012·Journal of the American Chemical Society·Tomoki OgoshiTada-aki Yamagishi
Apr 19, 2012·Nature Communications·Sara PasqualeJavier de Mendoza
May 1, 2012·Journal of the American Chemical Society·Guocan YuFeihe Huang
Feb 19, 2013·Chemistry : a European Journal·Severin T SchneebeliJ Fraser Stoddart
Aug 6, 2013·Journal of the American Chemical Society·Drew A FowlerJerry L Atwood
Apr 23, 2014·Chemical Communications : Chem Comm·Tomoki OgoshiTada-Aki Yamagishi
Jan 1, 2015·Chemical Science·Huanqing ChenChunju Li
Citations
Jun 24, 2016·Chemical Reviews·Tomoki OgoshiYoshiaki Nakamoto
Apr 27, 2017·The Journal of Physical Chemistry. a·Dipali N LandeShridhar P Gejji
Jul 1, 2017·Organic Letters·Yossi Zafrani, Yoram Cohen
Jan 10, 2018·Chemistry : a European Journal·Zhaozheng YangPeng Yang
Oct 27, 2017·Chemical Communications : Chem Comm·Lu DaiChunju Li
Apr 6, 2016·Chemical Communications : Chem Comm·Bo GaoYing-Wei Yang
Dec 15, 2015·Chemical Communications : Chem Comm·Jiong ZhouGuocan Yu
Sep 22, 2018·Chemistry : a European Journal·Denan WangRajendra Rathore
Jan 11, 2019·Chemical Communications : Chem Comm·Jia-Rui Wu, Ying-Wei Yang
Jun 19, 2019·Chemical Communications : Chem Comm·Hongxin ChaiWei Jiang
Nov 26, 2019·Angewandte Chemie·Weiwei YangAndrew C-H Sue
Feb 8, 2020·Angewandte Chemie·Clément ChauvierMartin Oestreich
Nov 6, 2018·Chemical Science·Shohei TashiroMitsuhiko Shionoya
May 1, 2016·Chemical Science·J E M LewisS M Goldup
Dec 28, 2019·Journal of Chemical Information and Modeling·Rabindranath Paul, Sandip Paul
Mar 2, 2021·Organic Letters·Jing ZhaoHuan Li
May 6, 2021·Chemical Communications : Chem Comm·Dingsheng ZhuHao Li
Oct 21, 2016·Chemistry, an Asian Journal·Suxiang MaChunju Li
Mar 7, 2018·Journal of Medicinal Chemistry·Lijun SongSerge Van Calenbergh
Dec 10, 2016·Inorganic Chemistry·Michał J BiałekLechosław Latos-Grażyński
Oct 29, 2019·Organic Letters·Ming LiBin Hua
Aug 12, 2021·Angewandte Chemie·Jing LiChuan-Feng Chen
Nov 10, 2020·Journal of the American Chemical Society·Yitao WuFeihe Huang
Aug 25, 2017·The Journal of Organic Chemistry·San-Jiang PanWei Jiang
Aug 22, 2020·Organic Letters·Monika Chwastek, Agnieszka Szumna
Nov 3, 2021·Chemical Communications : Chem Comm·Qiang ShiLeyong Wang