Temperature-dependent isomerisation versus net fragmentation of secondary allylic alcohols with Grubbs' catalyst

MK Gurjar, P Yakambram

Index: Gurjar, Mukund K.; Yakambram, Pedduri Tetrahedron Letters, 2001 , vol. 42, # 21 p. 3633 - 3636

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Citation Number: 69

Abstract

Secondary allylic alcohols with 10 mol% of Grubbs catalyst in refluxing toluene/1, 2- dichloroethane undergo isomerisation to ethyl ketones whereas with 100 mol% of Grubbs catalyst at room temperature, a net fragmentation reaction with the loss of a carbon atom occurs, to provide a methyl ketone. Probable mechanisms are described.