Journal
ORGANIC LETTERS
Volume 3, Issue 3, Pages 425-428Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol006931x
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[GRAPHICS] alpha -Amino alpha'-fluoro ketones are shown to be inherently unstable intermediates. Evidence is presented that they undergo enolization toward the amino group followed by expulsion of fluoride ion, forming a proposed oxyvinyliminium ion (amino-substituted oxyallyl cation). In protic, nucleophilic media the proposed intermediate is trapped by solvent. In the presence of a reactive diene, [4 + 3] cycloadducts have been isolated. Prior observations concerning fluorinated amino ketones are discussed in light of these findings.
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