3,4-Ethylenedioxythiophene and 3,4-ethylenedioxyselenophene: synthesis and reactivity of C(alpha)-Si bond.

A synthetic approach to synthesize EDOT and EDOS from a common precursor 5 is reported. The method involves zirconocene dichloride mediated reaction of a common diyne 5 followed by treatment with disulfur dichloride (S(2)Cl(2)) and in situ prepared selenium dichloride (SeCl(2)). The higher lability of alpha-trimethylsilyl group in EDOS compared to EDOT is explained using DFT calculations.