Beilstein J. Org. Chem.2016,12, 1467–1475, doi:10.3762/bjoc.12.143
properties (Fuel Dehydrating Icing Inhibitors - FDII). To this end, a kinetic appraisal of the hydrolysis reactions of representative geminal ethers was undertaken using a convenient surrogate for the fuel–water interface (D2O/CD3CN 1:4). We present here a library of acyclic and five/six-membered cyclic
geminal ethers arranged according to their hydroxonium catalytic coefficients for hydrolysis, providing for the first time a framework for the development of FDII. A combination of 1H NMR, labelling and computational studies was used to assess the effects that may govern the observed relative rates of
hydrolyses.
Keywords: FDII; geminal ethers; kinetics; Introduction
Our interest in organic dehydrating agents for applications in the aeronautical industry is stimulated by the commercial case for developing a new approach to managing water contamination in jet fuel. The acid-catalysed hydrolysis reactions
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Graphical Abstract
Scheme 1:
The three-stage mechanism for the specific acid-catalysed hydrolysis of cyclic orthoester A.