Abstract
Complexes of the type [Rh(diphosphine) (solvent) 2 ] + in dry acetone or tetrahydrofuran solutions are effective catalysts for generating synthetically useful quantities of simple enols from their corresponding allylic alcohols. A representative collection of simple enols has been produced, and the physical properties and stabilities are recorded. Although these catalysts also ketonize (tautomerize) the enols to their corresponding aldehydes and ketones, the simple enols are conveniently stable in solutions containing the milder catalysts. The mechanism of catalysis has been inferred from specific isotopic labeling experiments. The conclusions are as follows: the production of enols involves a hydrogen 1,3-shift mechanism involving hydrido-π-allylic intermediate. This process is also irreversible, and the stereoselective step is the α-hydrogen abstraction from the allylic substrate
Published Version
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