Lithium metal reduction annulenes

Reduction of the nonaromatic polyene [12]annulene, either electrochemically or with lithium metal, generates a 14-7c-electron dianion" ... 

The reduction of several annelated corannulene derivatives has been performed using lithium and potassium metals.7 It has been found that annelation affects the annulenic character of corannulene by changing its charge distribution the dianions of derivatives that are annelated with six-membered rings have less annulenic character and are less paratropic than corannulene dianion. 

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