[Reaction: see text] The transformation of 1,5-cyclooctadiene (1) into cyclooctatetraene (3) by way of dianion 2 is an interesting reaction of considerable preparative value. The mechanism was initially suggested to involve lithium hydride loss from 4a/4b, followed by two deprotonations to produce 2. This No-D 1H NMR study indicates the long-term stability of 4a/4b (in the absence of additional n-BuLi) and suggests a different mechanistic sequence, in which 4a/4b is deprotonated a second time prior to LiH ejection.
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