New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes

Seiji Shinkai, Koji Araki, Takayuki Tsubaki, Takashi Arimura, Osamu Manabe

Research output: Contribution to journalArticle

190 Citations (Scopus)

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 languageEnglish
Pages (from-to)2297-2299
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - Dec 1 1987
Externally publishedYes

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Calixarenes
Nitration
Nitric Acid
Solubility
Oxidation
Electrons
Water

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Shinkai, S., Araki, K., Tsubaki, T., Arimura, T., & Manabe, O. (1987). New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes. Journal of the Chemical Society, Perkin Transactions 1, 2297-2299.

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 journalArticle

Shinkai, S, Araki, K, Tsubaki, T, Arimura, T & Manabe, O 1987, 'New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes', Journal of the Chemical Society, Perkin Transactions 1, pp. 2297-2299.
Shinkai, Seiji ; Araki, Koji ; Tsubaki, Takayuki ; Arimura, Takashi ; Manabe, Osamu. / New syntheses of calixarene-p-sulphonates and p-nitrocalixarenes. In: Journal of the Chemical Society, Perkin Transactions 1. 1987 ; pp. 2297-2299.
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