Reactions of Aldehydes and Ketones and their Derivatives

Abstract

Formation and Reactions of Acetals and Related SpeciesThe α,α -dihaloketone 2,4-dichlorobicyclo[3.2.1]oct-6-en-3-one (1, a mixture of ax-ax, ax-eq, and eq-eq isomers) undergoes a 1,3-transposition in alkoxide-alcohol media to give α-ketoacetals (2, R = CH 3 , CH 2 CF 3 , −CH 2 CH 2 −), all of which are readily hydrolysable to the corresponding α-diones. 1 The acetal is favoured by an O,O-geminal stabilization relative to the α,α -dialkoxy ketone: none of the latter