Reactions of Alkyl β‐Nitroacrylates with Arenes in Triflic Acid: Synthesis of Oximes of Alkyl 2,3‐Diaryl‐3‐oxopropanoates
Year: 2023
Type: article
Abstract: Methyl or ethyl 3‐nitropropenoates (β‐nitroacrylates) AlkO(O)C 1 −C 2 H=C 3 H−NO 2 in reaction with arenes ArH in triflic acid CF 3 SO 3 H (TfOH) at room temperature in 1 h give rise to oximes of alkyl 2,3‐diaryl‐3‐oxopropanoates AlkO(O)C−CH(Ar)−C(Ar)=NOH in yields of 42–92 %. The obtained oximes bearing ortho ‐methyl substituents in the aryl ring exist as atropoisomers in solutions. The study of protonated forms of β‐nitroacrylates by NMR and DFT calculations has revealed that the reactive electrophiles are species AlkO(HO + )C 1 −C 2 H=C 3 H−N + (O)(OH) protosolvated on the acceptor groups NO 2 and CO 2 R. Plausible reaction mechanism is based on the primary interaction of aromatic nucleophiles with these electrophilic species onto their carbon C 2 .
Source: ChemistrySelect
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4387777942