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The puckered tricyclic heterocycle 6,12‐diphenyldibenzo[b,f][1,5]diazocine, a novel probe for revealing single‐electron transfer (SET) reactions, is here employed as a model substrate for investigating the carbolithiation of imines and the stereochemistry, the regiochemistry, and the electronic nature (polar or SET) of such R–Li additions. The chemical behavior of the following organolithium reagents...
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