Synthesis and Novel Rearrangement of 1, 1, 1-Trichloro-2-alken-4-ones

E Kiehlmann, PW Loo, BC Menon…

Index: Kiehlmann,E. et al. Canadian Journal of Chemistry, 1971 , vol. 49, p. 2964 - 2976

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Citation Number: 8

Abstract

Strong mineral acids convert 1, 1, 1-trichloro-2-hydroxy-4-alkanones to 1, 1, 1-trichloro-2- aIken-4-ones and 1, 1, 5-trichloro-1-alken-4-ones via an intramolecular chlorine shift from C- 1 to-5 of an enol allylic system. Alternatively, 1, 1, 1-trichloro-2-alken-4-ones may be synthesized from 1, 1, 1-trichloro-2-hydroxy-4-alkanones by acetylation and elimination of acetic acid or by nucleophilic substitution with thionyl chloride followed by ...