Abstract
Addition of triethylaluminium, ethyllithium, and ethylmagnesium bromide to 2,4,6-cyclooctatrien-1-one proceeded principally in a 1,2-manner. The subsequent work-up caused ring cleavage to yield 4,6,8-decatrien-3-one. Lithium diethylcopper gave a 1,4-adduct, 7-ethylcycloocta-3,5-dien-1-one (66%). The presence of hexamethylphosphoramide (HMPA) brought about a marked increase of the proportion of 1,4-adduct in the reactions of ethyllithium and ethylmagnesium bromide. The results were discussed together with the reactions of other α,β -unsaturated ketones under similar reaction conditions.
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