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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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No-D NMR study of the pathway for n-BuLi "oxidation" of 1,5-cyclooctadiene to dilithium cyclooctatetraene dianion [Li2COT2-].

[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.[1]

References

  1. No-D NMR study of the pathway for n-BuLi "oxidation" of 1,5-cyclooctadiene to dilithium cyclooctatetraene dianion [Li2COT2-]. Hoye, T.R., Kabrhel, J.E., Hoye, R.C. Org. Lett. (2005) [Pubmed]
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