Coe, Paul L. published the artcileReactions of tetrafluoroethene oligomers. Part 15. Reactions of perfluoro-3,4-dimethylhex-3-en-2-one; a highly reactive α,β-unsaturated ketone, Computed Properties of 360-92-9, the publication is Perkin 1 (2000), 1529-1535, database is CAplus.
Perfluoro-3,4-dimethylhexenone I has been shown to react with nucleophiles both at the double bond and at the carbonyl group depending on the type of nucleophilic center and also on the steric requirements of the attacking reagent. In many cases the first formed product undergoes further reactions either with the original nucleophile or by intramol. processes. Thus, reaction of I with primary amines afforded azetines II (R = Et, c-C6H11, Me3C); with Me3CNH2, a mixture of an azetine II (R = Me3C) and a ketenimine III was formed. III either on standing at room temperature or more quickly on heating cyclized quant. to II (R = Me3C). Reaction of the enone with secondary amines took a different course; the products from reaction with diethylamine were an unsaturated amide and N,N-diethyltrifluoroethanamide, and piperidine afforded not only an unsaturated amide and the corresponding ethanamide but also a piperidyl ketone IV. IV is postulated to be the archetype of the first formed product for all the reactions reported. Reaction with dimethylamine yielded a different product, a disubstituted unsaturated ketone, but none of the corresponding amides as seen with other secondary amines. The reaction with hydrazine afforded a substituted pyrazolidine V. When the enone was treated either with triethylamine or with fluoride ion cyclization to yield a perfluorotetramethyldihydrofuran VI occurred. Reaction with sodium methoxide or sodium phenoxide yielded bis-ether derivatives, while reaction with sodium hypochlorite gave a hydrogen containing epoxide, postulated to arise from a haloform type reaction from the first formed epoxide. Finally, reaction with methylmagnesium iodide gave a fluoroethylidene trifluoromethylhexanone derivative A mechanistic rationale based on a series of addition-elimination reactions with or without subsequent cyclization is proposed to explain these reactions.
Perkin 1 published new progress about 360-92-9. 360-92-9 belongs to amides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Amine,Aliphatic hydrocarbon chain,Amide, name is N,N-Diethyl-2,2,2-trifluoroacetamide, and the molecular formula is C6H10F3NO, Computed Properties of 360-92-9.
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https://en.wikipedia.org/wiki/Amide,
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