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Dolbier HW Solutions 392 - 486 ENOLS AND ENOLATES 18.29(a...

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18.29 ( a ) The fi rst conversion is the halogenation of an aldehyde. As described in Section 18.2, this particular conversion has been achieved in 80% yield simply by treatment with bromine in chloroform. Dehydrohalogenation of this compound can be accomplished under E2 conditions by treat- ment with base. Sodium methoxide in methanol would be appropriate, for example, although almost any alkoxide could be employed to dehydrohalogenate this tertiary bromide. As the reaction was actually carried out, the bromide was heated with the weak base N , N -diethylaniline to effect dehydrobromination in 71% yield. ( b ) Cleavage of vicinal diols to carbonyl compounds can be achieved by using periodic acid (HIO 4 ) (Section 15.12). The conversion of this dialdehyde to cyclopentene-1-carbaldehyde is an intramolecular aldol condensation and is achieved by treatment with potassium hydroxide.
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