Path to Industrial Production of Calix[8 and 4]arenes

Haase, Cornelius

doi:10.1021/acs.joc.9b02692

Cited by 1 publication

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References 10 publications

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“…As a result, these molecules can be selectively functionalized at either rim and they can serve as building blocks for a variety of applications, such as, for example, ionic or molecular receptors. Gutsche and coworkers pioneered and developed methodologies for synthesizing p-tert-butylcalix [4]arene 3a [6] (also commonly and inaccurately referred to simply as "calix [4]arene", which should strictly be confined to the de-tert-butylated derivative of 3a), p-tert-butylcalix [5]arene 3b [7], p-tert-butylcalix [6]arene 3c [8], and p-tert-butylcalix [8]arene 3d [9] (recently, Haase reported a highly selective and high-yield synthesis for the production of calix [8]arenes [10]) as major products. Gutsche's syntheses were achieved using p-tert-butylphenol and formaldehyde under different but reproducible reaction conditions, which have allowed these compounds, and derivatives thereof, to become easily accessible to be widely studied.…”

Section: Introductionmentioning

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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