Volume 18, Issue 35
Preparative Organic Chemistry
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ChemInform Abstract: Metal-Assisted Reactions. Part 19. Burst Kinetics in Heterogeneous Catalytic Transfer Hydrogenolysis.

R. A. W. JOHNSTONE

R. A. W. JOHNSTONE

Dep. Org. Chem., Univ. Liverpool, Liverpool, L69 3BX, UK

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P. J. PRICE

P. J. PRICE

Dep. Org. Chem., Univ. Liverpool, Liverpool, L69 3BX, UK

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First published: September 1, 1987

Abstract

Arene (II) formation by catalytic transfer hydrogenolysis of aryloxytetrazolyl ethers (I) in the liquid phase using NaH2PO2-H2O as H donor shows biphasic concentration-time curves which indicate rate-limiting dissociation of heterogeneous complexes between catalyst and one of the reaction products, a tetrazolone (given in the scheme as its tautomer (III)).

ChemInform Abstract

Arene (II) formation by catalytic transfer hydrogenolysis of aryloxytetrazolyl ethers (I) in the liquid phase using NaH2PO2-H2O as H donor shows biphasic concentration-time curves which indicate rate-limiting dissociation of heterogeneous complexes between catalyst and one of the reaction products, a tetrazolone (given in the scheme as its tautomer (III)). A dependence of the catalytic reaction rate on pH and the hydrogenolysis of some modified ethers (IV) and (V) are also reported. In the case of (Ia) (R1: -O-Me) the effect of the catalyst modified with Pb is studied as well. The synthesis of all starting ethers (I), (IV), and (V), and of some preceding compounds is described.

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