Transmission of Substituent Effects through Oxygen and Sulfur Atoms. II. 13C Chemical Shifts of Ring-Substituted Phenyl Vinyl Ethers and Sulfides

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Abstract
The 13C chemical shifts of ring-substituted phenyl vinyl ethers and sulfides were measured and discussed in relation to the change in electron distribution caused by the ring-substitution. The Hammett plots of the shifts for the terminal carbon confirm the greater transmission efficiency of sulfur atom. An “inverse” substituent effect was found for the α-carbon of both compounds. This suggests that the bond-polarization plays an important role in the transmission of electronic effect.