Stereocontrolled oxidation of a thiacalix[4]arene to the sulfinyl counterpart of a defined S=O configuration

Naoya Morohashi, Nobuhiko Iki, Chizuko Kabuto, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

Treatment of p-tert-butylthiacalix[4]arene (1) with benzyl bromide in THF-DMF using Nail as the base catalyst afforded the tetrabenzyl ether of cone conformation (4(C)) as the major product, oxidation of which, with NaBO3 in CHCl3-acetic acid, proceeded readily to give the corresponding sulfinyl compound (5) with the four S=O groups disposed on the same side of the plane defined by the macrocyclic ring probably to avoid the steric hindrance imposed by the benzyllic moieties. Cleavage of the ether bonds gave a new stereoisomer of p-tertbutylsulfinylcalix[4]arene (2(ccc)) with the four S=O groups arranged in a cis-cis-cis configuration. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)2933-2937
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number16
DOIs
Publication statusPublished - 2000 Apr 15

Keywords

  • Calixarenes
  • Oxidation
  • Sulfinyl compounds
  • X-ray crystallography

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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