Abstract Base-induced or reductive cleavage of isoxazole rings followed by silylation of the resulting open-chain products affords bis (siloxy) butadienes in high yields. Their synthetic usefulness in the construction of multifunctionalized aromatic systems, via Diels-Alder reactions, is shown. The ability of bis (siloxy) butadienes to undergo deprotonation and reaction with electrophiles is also studied.