Abstract
Abstract Et2AlCH2AlEt2 (1) has been used as a mechanistic probe to determine the nature of the transition state in the reaction of two equivalents of a trialkylaluminum compound with a ketone in hydrocarbon solvent.1 was prepared in benzene and the solution composition determined. Low temperature1H NMR data of1 as the mono(diethyl etherate) indicate that the ether oxygen is simultaneously coordinated to both aluminum atoms. The reactions of1 with 4-t-butylcyclohexanone in hydrocarbon solvent were compared to the reactions of triethylaluminium with the same ketone. The results support the importance of a bridging alkyl group described by the formation of a six-centered transition state when two equivalents of a trialkylaluminum compound are allowed to react with a ketone in hydrocarbon solvent. The results also argue against a transition state described by two moles of trialkylaluminum compound complexed to the carbonyl oxygen atom.
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