32830-75-4Relevant academic research and scientific papers
Characterization and stereochemistry of alkyl 2-chloro-3-formylacrylates: Experimental NMR and theoretical DFT studies
Barhoumi-Slimi,Dhia, M. T. Ben,Nsangou,El Gaied,Khaddar
, p. 251 - 257 (2010)
The synthesis of alkyl 2-chloro-3-formylacrylates 1 from alkyl pyruvates was carried out using Vilsmeier reaction. The reaction is highly stereoselective and leads to a 95:5 mixture of Z and E stereoisomers. Both stereoisomers were characterized by 1H and 13C NMR. In CDCl3 solution, the NMR data, particularly the NOEDIFF experiments, show that the major species formed is the Z stereoisomer. Heating compound 1 in THF at reflux afforded the cyclic product 2 in 90 % yield. The interpretation of the experimental data were further supported by DFT/B3LYP calculations.
