Indole or 1-(trimethylsily1) indole was reacted sequentially with lithium-chlorotrimethylsilane and with 1, 4-benzoquinone to produce 1, 4-bis (trimethylsilyl) indole (50% and 55%, respectively). Methanolysis gave 4-(trimethylsily1) indole which reacted with electrophiles at C-3. However, the derivative l-acetyl-4-(trimethylsily1) indole reacted with acetyl, 2- chloropropanoyl, or propenoyl chlorides via clean C-4 ipso substitution. Attempts to ...
