Treatment of compound A with sodium amide converts it to compound B. Compound B on ozonol-ysis gives a diacid that retains all the carbon atoms of B. Compound B must therefore be a cyclicalkyne, formed by an intramolecular alkylation.Compound B is cyclotetradecyne.Hydrogenation of compound B over Lindlar palladium yieldscis-cyclotetradecene (compound C).Hydrogenation over platinum gives cyclotetradecane (compound D).Sodium–ammonia reduction of compound B yields trans-cyclotetradecene.The cis and trans isomers of cyclotetradecene are both converted to O?CH(CH2)12CH?O onozonolysis, whereas cyclotetradecane does not react with ozone.
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