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Controlled Synthesis of Mono‐ p ‐[(2,3‐epoxy)propyl]‐ and Mono‐ p ‐(2‐oxoethyl)‐tris‐ p ‐ tert ‐butylcalix[4]arenes Crystal Structure Determination of an Epoxy Calix[4]arene
Author(s) -
Berthalon Sandrine,
MottaViola Laure,
RegnoufdeVains JeanBernard,
Lamartine Roger,
Lecocq Sylvain,
Perrin Monique
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199909)1999:9<2269::aid-ejoc2269>3.0.co;2-3
Subject(s) - chemistry , epoxy , epoxide , calixarene , tris , crystal structure , stereochemistry , polymer chemistry , medicinal chemistry , crystallography , organic chemistry , molecule , catalysis , biochemistry
Abstract Four new tri‐ tert ‐butylcalix[4]arenes bearing an epoxy or a carbaldehyde function at the upper rim have been prepared by a multi‐step synthetic pathway involving initial selective allylation of tris‐( O ‐benzoyl)‐tri‐ tert ‐butylcalix[4]arene, followed by either m ‐CPBA oxidation or ozonolysis of the allyl group. The benzoylated epoxycalixarene was obtained as single crystals, analysis of which confirmed the formation of the epoxide group and the partial‐cone conformation of the macrocyclic structure.