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 language | English |
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Pages (from-to) | 2933-2937 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 41 |
Issue number | 16 |
DOIs | |
Publication status | Published - 2000 Apr 15 |
Keywords
- Calixarenes
- Oxidation
- Sulfinyl compounds
- X-ray crystallography
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry