The Influence of the 2-Alkoxy Group and of C-5 Substituents on the Direction of Reductive Cleavage of 2-Alkoxytetrahydrofurans by AlH2Cl in Ether Solution

PC Loewen, MLP Makhubu…

Index: Loewen,P.C. et al. Canadian Journal of Chemistry, 1972 , vol. 50, p. 1502 - 1512

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Citation Number: 11

Abstract

The AlH2Cl hydrogenolysis of ether solutions of 2-alkoxytetrahydrofurans in which the alkoxy group is either CH3O, C2H5O, i-C3H7O, or t-C4H9O, gives only those products resulting from ring CO bond cleavage. However, substituents at C-5 of 2- methoxytetrahydrofuran exert a strong effect on the ratio of ring to exo CO bond cleavage. Thus, alkyl (electron donor) groups at C-5 promote an increase in the amount of exo ...