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

Beilstein J Org Chem

Bayer AG, Research & Development Crop Science, Industriepark Höchst, 65926 Frankfurt, Germany.

Published: February 2021

A novel reactivity of 1,1,1-trifluoroalkanones is reported, where the reaction with AlCl results in the formation of 1,1-dichloro-1-alkenones. The reaction scope was found to be broad, with various chain lengths and aryl substituents tolerated. For substrates containing an electron-rich aromatic ring, further reactions take place, resulting in bicyclic and/or rearrangement products.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884876PMC
http://dx.doi.org/10.3762/bjoc.17.36DOI Listing

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