No-D NMR pstudy of the pathway for n-BuLi "oxidation" of 1,5-cyclooctadiene to dilithium cyclooctatetraene dianion [Li 2COT2-]

Thomas R Hoye, James E. Kabrhel, Rebecca C. Hoye

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Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)275-277
Number of pages3
JournalOrganic Letters
Volume7
Issue number2
DOIs
StatePublished - Jan 20 2005

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