| Abstract: | Stereochemistry of the Reformatsky Reaction of 2-Alkylcyclohexanones with Ethyl α-(Bromomethyl)acrylate A relation between the chemical shifts of the 13C-NMR signals of the carbon atoms 4, 5 and 9 and the conformation of the lactone oxygen was found for spiro-α-methylene-γ-butyrolactones prepared by the Reformatsky reaction of 2-alkylcyclohexanones with ethyl α-(bromomethyl)acrylate. It was confirmed by CD measurements on the pyrazoline derivative of one of the lactones. From the structures of the reaction products it was deduced, that trans addition (relative to the substituent at position 2) of the organometallic reagent is prefered. |
