The 1H n.m.r. spectra of solutions of succinaldehyde, glutaraldehyde, and adipaldehyde in deuterium oxide have been studied. At room temperature, the major component of solutions of succinaldehyde and glutaraldehyde is a cyclic monohydrate which is accompanied by the free aldehyde OCH·CH2·[CH2]n·CH2CHO, the acyclic monohydrate (DO)2CH·CH2·[CH2]n·CH2·CHO, and the dihydrate (DO)2CH·CH2·[CH2]n·CH2·CH(OD)2; at higher temperatures the free aldehyde content increases, mainly at the expense of the cyclic monohydrate. Adipaldehyde, by contrast, forms only the acyclic dihydrate. Although the undiluted aldehydes polymerise readily, their neutral aqueous solutions are stable for Iong periods; acidification induces rapid polymerisation. A common mechanism is suggested for hydration and polymerisation.
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Journal of the Chemical Society, Perkin Transactions 2
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