Characterization and stereochemistry of alkyl 2-chloro-3-formylacrylates: Experimental NMR and theoretical DFT studies

TM Barhoumi-Slimi, MTB Dhia, M Nsangou…

Index: Barhoumi-Slimi; Dhia, M. T. Ben; Nsangou; El Gaied; Khaddar Journal of Structural Chemistry, 2010 , vol. 51, # 2 p. 251 - 257

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Citation Number: 3

Abstract

Abstract 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 1 H and 13 C NMR. In CDCl 3 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 ...