Orientation in the Crossed Aldol Condensation of Chloral with Unsymmetrical Aliphatic Ketones

E Kiehlmann, PW Loo

Index: Kiehlmann,E.; Loo,P.-W. Canadian Journal of Chemistry, 1971 , vol. 49, p. 1588 - 1597

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Citation Number: 7

Abstract

The reactivity of a series of 14 aliphatic ketones in the crossed aldol condensation with chloral has been studied in glacial acetic acid and in dimethoxyethane. The reaction is irreversible and not accompanied by dehydration of the resulting 1, 1, 1-trichloro-3-hydroxy- 4-alkanones. Except for butanone, condensation occurs preferentially at the least-hindered position of an unsymmetrical ketone. The α-methyl/α-methylene condensation product ...