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paraldehyde : ウィキペディア英語版
paraldehyde

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Paraldehyde is the cyclic trimer of acetaldehyde molecules. Formally, it is a derivative of 1,3,5-trioxane. The corresponding tetramer is metaldehyde. A colourless liquid, it is sparingly soluble in water and highly soluble in ethanol. Paraldehyde slowly oxidizes in air, turning brown and producing an odour of acetic acid. It quickly reacts with most plastics and rubber.
Paraldehyde was first synthesized in 1829 by Wildenbusch. It has uses in industry and medicine.
== Stereochemistry ==
Theoretically four stereoisomeric structures are possible. The structures (1) and (2) are known as cis- and trans-paraldehyde. The structures (3) (a conformer of (2)) and (4) (a conformer of (1)) don't exist for steric reasons.〔Kewley, R.: ''Microwave spectrum of paraldehyde'' in Can. J. Chem. 48 (1970), 852–855〕〔Carpenter, D.C., Brockway, L.O.: ''The Electron Diffration Study of Paraldehyde'' in J. Amer. Chem. Soc. 58 (1936), 1270–1273〕

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