Selectivity and mechanism in the microsomal benzylic hydroxylation

R Amodeo, E Baciocchi, M Crescenzi, O Lanzalunga

Index: Amodeo, Rachele; Baciocchi, Enrico; Crescenzi, Manuela; Lanzalunga, Osvaldo Tetrahedron Letters, 1990 , vol. 31, # 24 p. 3477 - 3480

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Citation Number: 12

Abstract

Abstract The oxidation by rat liver microsomes of 4-Z-1, 2-dimethylbenzenes (1) and 4- methoxybenzyltrimethylsilane (2) has been investigated. The reaction of the former substrates leads to the expected isomeric benzyl alcohols 3 and 4, with a very low intramolecular selectivity, and only O-demethylation is observed in the reaction of 2. These results suggest the operation of a hydrogen atom transfer mechanism.