Abstract
Calixarene-p-sulphonates (tetramer, hexamer, and octamer) have been prepared (75-88%) and used to give p-nitrocalixarenes (15-22% yields based on the starting calixarenes). The novel nitration has two advantages: (i) calixarenes are protected from nitric acid oxidation by the electron-withdrawing sulphonate groups and (ii) the difference in the water-solubility of the p-nitrocalixarenes from the sulphonate-containing, lower nitration products, allows ready isolation of the former. The p-nitrocalixarenes thus obtained have potential as intermediates in the synthesis of a variety of functionalised calixarenes.
| Original language | English |
|---|---|
| Pages (from-to) | 2297-2299 |
| Number of pages | 3 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Publication status | Published - Dec 1 1987 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
Cite this
New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes. / Shinkai, Seiji; Araki, Koji; Tsubaki, Takayuki; Arimura, Takashi; Manabe, Osamu.
In: Journal of the Chemical Society, Perkin Transactions 1, 01.12.1987, p. 2297-2299.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes
AU - Shinkai, Seiji
AU - Araki, Koji
AU - Tsubaki, Takayuki
AU - Arimura, Takashi
AU - Manabe, Osamu
PY - 1987/12/1
Y1 - 1987/12/1
N2 - Calixarene-p-sulphonates (tetramer, hexamer, and octamer) have been prepared (75-88%) and used to give p-nitrocalixarenes (15-22% yields based on the starting calixarenes). The novel nitration has two advantages: (i) calixarenes are protected from nitric acid oxidation by the electron-withdrawing sulphonate groups and (ii) the difference in the water-solubility of the p-nitrocalixarenes from the sulphonate-containing, lower nitration products, allows ready isolation of the former. The p-nitrocalixarenes thus obtained have potential as intermediates in the synthesis of a variety of functionalised calixarenes.
AB - Calixarene-p-sulphonates (tetramer, hexamer, and octamer) have been prepared (75-88%) and used to give p-nitrocalixarenes (15-22% yields based on the starting calixarenes). The novel nitration has two advantages: (i) calixarenes are protected from nitric acid oxidation by the electron-withdrawing sulphonate groups and (ii) the difference in the water-solubility of the p-nitrocalixarenes from the sulphonate-containing, lower nitration products, allows ready isolation of the former. The p-nitrocalixarenes thus obtained have potential as intermediates in the synthesis of a variety of functionalised calixarenes.
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M3 - Article
SP - 2297
EP - 2299
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 1472-7781
ER -