80152-55-2Relevant academic research and scientific papers
Substituent Effects in the Reaction of t-Butylmagnesium Chloride with Substituted Ethyl Cinnamates. A Correlation with 13C NMR Chemical Shifts
Jalander, Lars
, p. 419 - 428 (2007/10/02)
The reaction of t-butylmagnesium chloride with some substituted ethyl (E)-cinnamates gave mainly 1,3-, 1,4-, 1,2- and 1,4-addition products and minor amounts of 1,2- and 1,3-addition products.The relative amounts of 1,3-addition products has been shown to correlate with 13C NMR chemical shifts of C-α of the ethyl cinnamates.The correlation indicates that the regio selectivity of the reactions is to a great extent dependent of polar effects and that the t-butyl radical has a nucleophilic character.
