Issue 9, 2002

Saccharide-accelerated hydrolysis of boronic acidimines

Abstract

Twenty substituted N-benzylidineaniline derivatives have been synthesised and their kinetic behaviour investigated. The rate of hydrolysis of the boronic acid imines was found to be accelerated by added saccharide. Catalytic activity was only observed below the pKa of the boronic acid. Altering the concentration or type of saccharide revealed a Brønsted-like linear free energy relationship, indicating that intramolecular general acid catalysis was operating. Structure–activity relationship studies demonstrated that the system's electronic demands were independent of the boronic acid moiety.

Graphical abstract: Saccharide-accelerated hydrolysis of boronic acid imines

Article information

Article type
Paper
Submitted
19 Mar 2002
Accepted
18 Apr 2002
First published
23 Jul 2002

New J. Chem., 2002,26, 1228-1237

Saccharide-accelerated hydrolysis of boronic acid imines

J. H. Hartley, M. D. Phillips and T. D. James, New J. Chem., 2002, 26, 1228 DOI: 10.1039/B202793C

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