Abstract
Allylbenzene chromiumtricarbonyl complexes are deprotonated under several basic conditions: tBuOKTHF, NaHDMF and phase transfer catalysis. The regioselectivity of the addition of carbonyl compounds on the complexed allylic anions is influenced by the nature of the cations M +. With M + = K +, Na +, N +( nBu) 4 the reaction of aromatic aldehydes is under thermodynamic control: only the most stable alcohols, dienes or ketones are isolated. With M + = K +, ketones are formed by an in situ Oppenauer-Woodward oxidation. With M + = Li + the reaction is in great part under kinetic control. Benzaldehyde gives rise to a mixture of α and γ alcohols. With acetophenone and diethyl ketone the reaction is regiospecific. Only the linear alcohols are obtained. This result, different from that obtained in non-complexed series under similar conditions, is the consequence of the steric strain of the complexed benzenic nucleus.
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