The literature on preparation and oxidation of carbanions is reviewed. Attempted preparation of many new carbanions, using Lochmann's base (potassium t-butoxide/n-butyllithium), is described; dianions 59, 76, and 85 were prepared for the first time. Preparation of 85, calculated to have the least delocalization energy of all six-carbon acyclic carbanions, completes the series of six-carbon acyclic dianions. Reaction of these and three other dicarbanions (o-48, m-58, and p-58) with dihalides and oxidizing agents were investigated. The shortest routes to certain {n}- and {n,n}-cyclophanes resulted. Good yields were obtained of {9}- and -metacyclophane. Several {n}-2,6-pyridinophanes were synthesized from dianion 59. {6,6}- and {7,7}-metacyclophane and {5,5}-, {7,7}-, and {9,9}- orthocyclophane were synthesized for the first time.

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