Hemisphere-shaped calixarenes and their analogs: synthesis, structure, and chiral recognition ability

Sawada, Tsuyoshi; Hongo, Takuya; Matsuo, Naomi; Konishi, Masakazu; Kawaguchi, Tsutomu; Ihara, Hirotaka

doi:10.1016/j.tet.2011.04.025

Cited by 6 publications

(3 citation statements)

References 45 publications

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“…21 Besides classical calixarenes, also calixarenes containing modified meso bridges are known, 22 they are calixradialenes, 23 ketocalixarenes 24 and homocalixarenes. 25,26 The noncovalent calixarene assemblies with porphyrins [27][28][29] are recently the theme of a large amount of reports. 30 …”

Section: Introductionmentioning

confidence: 99%

Selected applications of calixarene derivatives

Deska¹,

Dondela²,

Śliwa³

et al. 2015

Arkivoc

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Section: Introductionmentioning

confidence: 99%

Selected applications of calixarene derivatives

Deska¹,

Dondela²,

Śliwa³

et al. 2015

Arkivoc

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“…It is presumed that the trihydroxy-diketo intermediate 21 is first formed, and then undergoes intramolecular TMSI-mediated cyclizations to form the observed products [ 39 , 40 , 41 ]. Sawada and co-workers had previously reported that the treatment of tetramethoxy [2.1.2.1]MCPs with TMSI formed hemisphere-shaped calixarene analogues containing a dihydrobenzofuran ring [ 42 , 43 ]. The CDCl 3 1 H-NMR spectrum of the symmetrical 22a shows the hydroxyl signal at δ 6.54 ppm, indicating intramolecular hydrogen bonding between the hydroxyl and the oxygen of one of the benzofuran rings.…”

Section: Calixbenzofuran-analogous Mcps: Calix[3]benzofuran Analogmentioning

confidence: 99%

Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

et al. 2020

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Calixarene-analogous metacyclophanes (CAMs) are a special class of cyclophanes that are cyclic polyaromatic hydrocarbons containing three or more aromatic rings linked by one or more methylene bridging groups. They can be considered to be analogues of calixarenes, since, in both types of molecules, the component aromatic rings are linked by methylene groups, which are meta to each other. Since the prototype or classical calix[4]arene consists of four benzene rings each linked by methylene bridges, which are also meta to each other, it can be considered to be an example of a functionalized [1.1.1.1]metacyclophane. A metacyclophane (MCP) that consists of three individual hydroxyl-group functionalized aromatic rings linked by methylene groups, e.g., a trihydroxy[1.1.1]MCP may therefore, by analogy, be termed in the broadest sense as a “calix[3]arene” or a “calix[3]arene-analogous metacyclophane”. Most of the CAMs reported have been synthesized by fragment coupling approaches. The design, synthesis and development of functionalized CAMs, MCPs, calixarenes and calixarene analogues has been an area of great activity in the past few decades, due their potential applications as molecular receptors, sensors and ligands for metal binding, and for theoretical studies, etc. In this review article, we focus mainly on the synthesis, structure and conformational properties of [1.1.1]CAMs, i.e., “calix[3]arenes” and their analogues, which contain three functionalized aromatic rings and which provide new scaffolds for further explorations in supramolecular and sensor chemistry.

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“…The mononitration product (cone-3c) was not obtained under any of the conditions they tested. 19 The selective ipso-nitration of tert-butyl [2.2.2]MCP through the use of fuming nitric acid or copper nitrate was reported in 2011 by Sawada et al 20 As detailed in that report, when 2,2',9,9'-tetra-t-butyl-5a,10b-dihydro- [ Obviously, the nature of the various substituents (R) plays a key role in the determination of the nitration positions in the ipso-nitration of calixarenes in traditional methods, when used nitric acid as nitrating agent. Redon et al explained a possible mechanism for this in their report.…”

Section: T-bu T-bumentioning

confidence: 99%

Recent advances in ipso-nitration reactions

Bozorov¹,

Zhao²,

Aisa³

et al. 2016

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In the present review the various types of ipso-nitration reactions, in particular those advances in ipsonitration reactions that have been reported since the beginning of this century (i.e., from [2000][2001][2002][2003][2004][2005][2006][2007][2008][2009][2010][2011][2012][2013][2014][2015] are discussed. The review highlights the recent developments of the ipso-nitration reactions, a variety of the differences between traditional and modern methods for performing ipso-nitration reactions, as well as the most novel approaches to performing these reactions. In addition, the proposed mechanisms of ipso-nitration reactions are discussed.

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Hemisphere-shaped calixarenes and their analogs: synthesis, structure, and chiral recognition ability

Cited by 6 publications

References 45 publications

Selected applications of calixarene derivatives

Selected applications of calixarene derivatives

Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

Recent advances in ipso-nitration reactions

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