Abstract
A coupling reaction between arylaldehydes and ethyl trichloroacetate is facilitated by PPh3 under mild conditions to stereospecifically produce (Z)-ethyl α-chloroacrylates. This stereospecific coupling reaction only occurs when the arylaldehyde derivative has an electron-withdrawing substituent. On the other hand, when an electron-donating group is present in the aromatic ring, the aryldichloromethyl derivative is formed as the only product, even at low temperature. The stereospecificity in the coupling reaction was established based on the coupling constants 2JCH and 3JCH in the 13C NMR and crystal-X-ray analysis. From this data we propose that the formation of these compounds occurs through two intermediates initially formed by the reaction between the PPh3 and ethyl trichloroacetate.
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