?-chlorovinylaldehydes as intermediates in the synthesis of new substituted ?–fluoroalkoxyvinyl aldehydes and corresponding alcohols

A convenient synthesis of a series new ?-fluoroalkoxyvinyl aldehydes and their corresponding alcohols from ?-chloro-?,?-unsaturated was developed. The etherification reaction the carbonyl reduction were successfully achieved, affording desired products in good yields. mechanism nucleophilic vinylic substitution 3-chloro-3-phenylacrylaldehyde has been studied using DFT methods. IRC analysis shows presence hidden intermediate, agreement with one kinetic step two-stage process. isomerization intermediate Z-3-chloro-3-phenylacrylaldehyde (IntZ) into E-3-chloro-3-phenylacrylaldehyde (IntE) explained terms small energy gap difference between two intermediates IntZ IntE thermodynamic stability stereoisomer E compared to Z.