Novel Calixarene Hemisphere Synthesized via Pinacol Rearrangement of [2.1.2.1]Metacyclophane

Sawada, Tsuyoshi; Nishiyama, Yousuke; Tabuchi, Wataru; Ishikawa, Makoto; Tsutsumi, Emi; Kuwahara, Yutaka; Shosenji, Hideto

doi:10.1021/ol060286y

Cited by 17 publications

(4 citation statements)

References 13 publications

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“…Calix[4]arenes with two bridges functionalized have been prepared by the fragment condensation method, by a homologous anionic ortho Fries rearrangement, via rearrangement of a metacyclophane derivative possessing two pinacol subunits, by a spirodienone route, or by annulation of a biscarbene complex . Calix[4]arenes with the bridges functionalized in two different fashions have been obtained by the fragment condensation method or via addition of PhLi or t -BuLi to a ketocalix[4]arene derivative. , Compared to the other approaches for the introduction of substituents at the bridges, the experimental conditions used for the route involving S N 1 substitution of the bromocalixarenes are remarkably simple.…”

Section: Introductionmentioning

confidence: 99%

Calix[4]arenes with Two Different Chemical Modifications at the Bridges

Kuno

Biali

2011

J. Org. Chem.

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Hexabromocalix[4]arene derivatives (3a and 3b) possessing pairs of dibromomethylene and bromomethylene groups located at distal or proximal positions of the calix scaffold were prepared via photochemical bromination of tetramethoxycalix[4]arene. The dibromomethylene groups undergo hydrolysis to afford calix[4]arenes possessing pairs of carbonyl groups and bromomethylene groups located at distal or proximal bridges (4a and 4b, respectively). The bromomethylene groups of 4 undergo reactions with nucleophiles under S(N)1 conditions to afford a wide array of derivatives possessing two different chemical modifications at the bridges.

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Section: Introductionmentioning

confidence: 99%

Calix[4]arenes with Two Different Chemical Modifications at the Bridges

Kuno

Biali

2011

J. Org. Chem.

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“…62 Another example of a homocalixarene is 19, obtained from diphenylmethane dialdehyde 20 using aluminum powder and sodium hydroxide. 63 Compound 19 has proven useful as a synthon for further reactions. 64 (Scheme 3) …”

Section: Methodsmentioning

confidence: 99%

Calixarenes containing modified meso bridges

Deska¹,

Dondela²,

Śliwa³

2014

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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Novel Calixarene Hemisphere Synthesized via Pinacol Rearrangement of [2.1.2.1]Metacyclophane

Cited by 17 publications

References 13 publications

Calix[4]arenes with Two Different Chemical Modifications at the Bridges

Calix[4]arenes with Two Different Chemical Modifications at the Bridges

Calixarenes containing modified meso bridges

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

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