Stereoselective oxidation of thiacalix[4]arenes with the NaNO3/CF3COOH system

Lhoták, Pavel; Morávek, J.; Šmejkal, Tomáš; Stibor, Ivan; Sýkora, Ján

doi:10.1016/s0040-4039(03)01868-9

Cited by 21 publications

(10 citation statements)

References 14 publications

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“…Regio-and stereoselective oxidation [73] enabled a collection of novel building blocks to be prepared. For example, the oxidation of 14b with NaNO 3 as the oxidizing agent gave the tetrasulfoxide 71 (containing the rctt configuration of sulfoxides) in 64 % yield.…”

Section: Reactions Involving the Bridging Groupsmentioning

confidence: 99%

Chemistry of Thiacalixarenes

2004

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Thiacalixarenes — new members of the calixarene family — are very promising molecules with many potential applications in supramolecular chemistry. The presence of four sulfur atoms in the place of methylene groups imparts many novel features and properties to these molecules. This review deals with the chemistry of thiacalixarenes, and by comparision with “classical” calixarenes, emphasizes their differences in reactivity, unusual conformational preferences and modified complexation abilities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Reactions Involving the Bridging Groupsmentioning

confidence: 99%

Chemistry of Thiacalixarenes

2004

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“…[5,7] A full characterization of 2-eeee [ 1 H and 13 C NMR, HRMS (ESI-TOF), HPLC] is reported below.…”

Section: Resultsmentioning

confidence: 99%

“…In this respect the stereoselective oxidation of thiacalix [4]arenes with the NaNO 3 /CF 3 CO 2 H system to obtain the corresponding tetrasulfinyl derivative has to be recalled. [5] When carried out on the cone-tetrapropoxytetra-state upon irradiation at a given wavelength. The order of appearance of the different isomers in the reaction mixture plays a key role in the disclosure of the identity of all the isomers of the PDCL.…”

Section: Introductionmentioning

confidence: 99%

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A Photodynamic Library of Tetrasulfinylcalix[4]arenes: The Sulfinyl Dance

et al. 2012

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The photoinversion of sulfoxides has been exploited to generate a photodynamic combinatorial library (PDCL) of tetrasulfinylcalix[4]arenes. Irrespective of the starting isomer, the same product distribution is obtained at the photostationary state upon irradiation at a given wavelength. The order of appearance of the different isomers in the reaction mixture plays a key role in the disclosure of the identity of all the isomers of the PDCL

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“…Sulphonylcalix[4]arene 71 could be received through oxidizing thiacalix[4]arene using the mixture of H 2 O 2 and NaBO 3 in acetic acid [54]. A series of alkyl substituted thiacalix [4]arene derivatives could be oxidized with NaNO 3 /CF 3 COOH and led to the corresponding tetrasulfoxides where alkyl and sulfoxide groups were oriented in the opposite directions in a stereoselective manner [57]. A series of alkyl substituted thiacalix [4]arene derivatives could be oxidized with NaNO 3 /CF 3 COOH and led to the corresponding tetrasulfoxides where alkyl and sulfoxide groups were oriented in the opposite directions in a stereoselective manner [57].…”

Section: Sone Et Al Reported the Synthesis Of P -T E R Tbutylthiacalmentioning

confidence: 99%