E/Z Isomerization of 3,3-disubstituted allylic thioethers

Allylic thioethers of the general structure 1 underwent E/Z isomerization during both basic and acidic hydrolysis of the ester moiety at the remote end of the molecule. The isomerization was dependent on the substitution of the allylic moiety. The presence of a 5-membered heterocycle on the double bond supported the isomerization. However, analogous oxy-ethers were stable.

E/Z Isomerization of allylic thioethers accompanies hydrolysis of the ester group. The isomerization depends on the substitution of the allylic moiety. Analogous allylic ethers are stable.