3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of Cα-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 (S2Cl2) and in situ prepared selenium dichloride (SeCl2). The higher lability of alpha-trimethylsilyl group in EDOS compared to EDOT is explained using DFT calculations.