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But-1-en-3-ynes react with lithium and chlorotrimethylsilane in THF to give 1,4-bis(trimethylsilyl)buta-2,3-dienes. Epoxidation of these allenes leads to oxyallyl species which are trapped by nucleophilic reagents to give 1,4-bis(trimethylsilyl)butan-3-ol-2-one derivatives.
AlCl 3 mediated acylation of 3-buten-1-yne derivatives with acyl chlorides yields a mixture of 5-chloro-2,3-pentadienones and 3-chloro-2,4-pentadienones. The proportion of allenylketones vs conjugated dienic ketones depends on the substitution pattern of the starting enyne. Acylation of 5-acetoxy-3-buten-1-ynes leads to the corresponding allenylketones (6-acetoxy-5-chloro-2,3-pentadienones).
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