In Situ Reduction and Functionalization of Polycyclic Quinones.

Attempts to functionalize polycyclic quinones using lithium diisopropylamide as a base led to the unexpected formation of acenes. This reaction proceeds by electron transfer from the base to the electron deficient quinone, whose radical anion can react with a variety of electrophiles. Siloxy derivatives synthesized by this method could be easily isolated but showed poor photostability. In situ reduced intermediate generation is a convenient approach to functionalization of oxidatively unstable hydroquinones.