Competitive Intermolecular Pericyclic Reactions of Free and Complexed Cyclopentyne

John C. Gilbert, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

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Intermolecular competition for cyclopentyne by different alkenes supports the hypothesis that organolithium-promoted decomposition of precursors to cyclopentyne affords one or more lithiumion-complexed species. Competition reactions with mixtures of 2,3-dihydropyran do not clearly differentiate between complexed and unencumbered (free) forms of cyclopentyne, but those involving spirodiene 2 and cyclohexene do. Remarkably, the cycloaddition reactions of free cyclopentyne are not diffusion-controlled despite its high reactivity.

Original languageEnglish
Pages (from-to)10067-10072
Number of pages6
JournalJournal of Organic Chemistry
Issue number26
StatePublished - 26 Dec 2003


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