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

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

Research output: Contribution to journalArticlepeer-review

225 Citations (Scopus)


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 - 1987
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry


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