Author:
Kiehlmann E.,Lehto N.,Cherniwchan D.
Abstract
The preparation and 1H and 13C nuclear magnetic resonance spectra of ten monoiodocatechin derivatives are described. The iodination of catechin with N-iodosuccinimide (NIS) takes place regiospecifically at C-6 in acetone but preferentially at C-8 in dimethylformamide; both products can be derivatized at oxygen in alkaline medium but lose iodine in the presence of acid. 3′,4′,5,7-Tetra-O-methylcatechin reacts with NIS regiospecifically at C-8 while catechin pentaacetate resists iodination. The debromination of 6-bromo- and 6,8-dibromocatechin with sodium sulfite in CD3CN/D2O is accompanied by H/D-exchange at C-6 and C-8. The synthesis of catechin pentaacetate from partially deuterated catechin and its conversion to tetra-O-methylcatechin proceed without H/D-exchange and permit distinction between the H-6 and H-8 chemical shifts.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
22 articles.
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