Newman–Kwart O→S rearrangement of di- and tetra(thiocarbamoyl)dinaphthylmethanes and octa(thiocarbamoyl)resorcinarenes

Tarasenko, D. V.; Serkova, O. S.; Vasyanina, L. K.; Maslennikova, V. I.

doi:10.1016/j.tetlet.2015.11.087

Cited by 8 publications

(2 citation statements)

References 25 publications

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“…In the first step, 5 is converted into tetra- O -thiocarbamate 6 . The applied conditions were adapted from related reactions on the resorcin[4]arene framework and optimized. Through the application of high-temperature microwave conditions, 6 is converted into the corresponding tetra- S -thiocarbamate via Newman–Kwart rearrangement.…”

mentioning

confidence: 99%

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?

Nemat

Tiefenbacher

2021

Org. Lett.

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Three novel thiol bearing resorcin [4]arene and pyrogallol[4]arene derivatives were synthesized. Their properties were studied with regards to self-assembly, disulfide chemistry, and Brønsted acid catalysis. This work demonstrates that (1) one aromatic thiol on the resorcin[4]arene framework is tolerated in the self-assembly process to a hexameric hydrogen bond-based capsule, (2) thio-derivatized resorcin[4]arene analogs can be covalently linked through disulfides, and (3) the increased acidity of aromatic thio-substituent is not sufficient to replace HCl as cocatalyst for capsule catalyzed terpene cyclizations.

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confidence: 99%

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?

Nemat

Tiefenbacher

2021

Org. Lett.

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“…17 In the first step, 5 is converted into tetra-O-thiocarbamate 6. The applied conditions were adapted from related reactions on the resorcin[4]arene framework 18 and optimized. Through the application of high-temperature microwave conditions, 19 6 is converted into the corresponding tetra-S-thiocarbamate via Newman-Kwart rearrangement.…”

mentioning

confidence: 99%

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are thiols tolerated in the self-assembly process?

Nemat

Tiefenbacher

2021

Preprint

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Three novel thiol bearing resorcin[4]arene and pyrogallol[4]arene derivatives were synthesized. Their properties were studied with regards to self-assembly, Brønsted acid catalysis, and disulfide chemistry. One new thiosubstituted macrocycle stands out in particular, as it forms a hexameric capsule in CDCl3 capable of terpene cyclizations, dimerizes via disulfide bridges under mild oxidative conditions, and most importantly shows guest uptake of both alkyl ammonium salts and C60-fullerenes.

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Molecular Rearrangements

Coxon¹

2020

Organic Reaction Mechanisms · 2016

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Newman–Kwart O→S rearrangement of di- and tetra(thiocarbamoyl)dinaphthylmethanes and octa(thiocarbamoyl)resorcinarenes

Cited by 8 publications

References 25 publications

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?

Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are thiols tolerated in the self-assembly process?

Molecular Rearrangements

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