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1 article(s) from Meister, Catherine S

Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

Beatrice Lansbergen,
Catherine S. Meister and
Michael C. McLeod

Beilstein J. Org. Chem. 2021, 17, 404–409, doi:10.3762/bjoc.17.36

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Graphical Abstract

Figure 1: Examples of biologically active 1,1-dichloro-1-alkenes.

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Figure 2: a) Common methods for the preparation of 1,1-dichloro-1-alkenes from aldehydes. b) This work: a two...

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Scheme 1: The initial attempt for the conversion of 1,1,1-trifluoroalkanone 5a to 1,1-dichloroalkenone 6a.

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Scheme 2: Substrate scope for the reaction of 1,1,1 trifluoroalkanones with AlCl₃. ^aPurification (normal or r...

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Scheme 3: Proposed mechanism for the formation of dichloroalkene 6 from trifluoroalkanone 5.

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Scheme 4: Formation of bicyclic ketones 9 and 10 from 1,1,1-trifluoroalkanone 5b using 7 equivalents of AlCl₃....

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Scheme 5: Conversion of 1,1,1-trifluoroalkanone 5n to acid chloride 13 with AlCl₃, and possible mechanism.

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Scheme 6: Conversion of 1,1,1-trifluoroalkane 16 to bicycle 17 upon treatment with AlCl₃, and possible mechan...

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Letter

Published 10 Feb 2021

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