Breaking thiacalix[4]arene into pieces – a novel synthetic approach to higher calixarenes bearing mixed (–S–, –CH<sub>2</sub>–) bridges

Kaiser, Lukáš; Landovský, Tomáš; Salvadori, Karolína; Eigner, Václav; Dvořáková, Hana; Lhoták, Pavel

doi:10.1039/d1ra07464d

Cited by 1 publication

(2 citation statements)

References 33 publications

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“…Tetramethoxy sulfoxide 3 was obtained in a 58% (1.03 g) yield as a white powder. All the data are in agreement with the literature [24]. 1 H NMR (CDCl 3 , 400 MHz, 298 K) δ 7.63 (bs, 2H, Ar-H), 7.56 (d, J = 2.5 Hz, 2H, Ar-H), 7.43 (bs, 4H, Ar-H), 3.78 (s, 6H, -O-CH 3 ), 3.46 (s, 6H, -O-CH 3 ), and 1.23 (s, 36H, tBu) ppm.…”

Section: Tetramethoxy Sulfoxide Derivativesupporting

confidence: 92%

“…The starting thiacalix [4]arene 1 was first alkylated to the corresponding tetramethyl derivative 2 (Scheme 1) following a published procedure [23]. The oxidation of this compound using sodium perborate produced a mixture of mono-and di-sulfoxides [24]. The required product 3 was obtained using column chromatography on a silica gel in a 58% yield.…”

Section: Resultsmentioning

confidence: 99%

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The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

Mamleev,

Eigner,

Dvořáková

et al. 2023

Molecules

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Thiacalix[4]arene monosulfoxide 4 possesses a very unusual chemistry, as demonstrated by several unprecedented derivatives in calixarene chemistry. Interestingly, compound 4 cannot be prepared by the dealkylation of its corresponding tetramethoxy derivative using BBr3. Instead, the borate complex is formed with a boron bound by the two neighboring phenolic oxygens and a sulfoxide group. A similar type of borate complex with a spirodienone fragment was then isolated as a by-product. The oxidation of monosulfoxide with Chloramine-T did not provide the expected spirodienone moiety, but rather a complex oxathiane-based spiroheterocyclic part containing a chlorine atom. X-ray analyses confirmed the structures of the unusual products and feasible formation mechanisms were proposed. These results provide further evidence of the distinction between thiacalixarene chemistry and the chemistry of classical CH2 analogues.

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Section: Tetramethoxy Sulfoxide Derivativesupporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

Mamleev,

Eigner,

Dvořáková

et al. 2023

Molecules

Self Cite

View full text Add to dashboard Cite

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Breaking thiacalix[4]arene into pieces – a novel synthetic approach to higher calixarenes bearing mixed (–S–, –CH₂–) bridges

Abstract: A novel approach is based on the cleavage of thiacalix[4]arene monosulfoxide with BuLi providing a linear tetramer in an essentially quantitative yield which is used as a building block for further cyclization.

Cited by 1 publication

References 33 publications

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

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Breaking thiacalix[4]arene into pieces – a novel synthetic approach to higher calixarenes bearing mixed (–S–, –CH2–) bridges

Abstract: A novel approach is based on the cleavage of thiacalix[4]arene monosulfoxide with BuLi providing a linear tetramer in an essentially quantitative yield which is used as a building block for further cyclization.

Cited by 1 publication

References 33 publications

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide

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Breaking thiacalix[4]arene into pieces – a novel synthetic approach to higher calixarenes bearing mixed (–S–, –CH₂–) bridges