Pericyclic reactions of free and complexed cyclopentyne

John C. Gilbert, Duen Ren Hou, Julian W. Grimme

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The selectivity between [2 + 2] and [2 + 4] cycloadditions of cyclopentyne with spiro[2.4]nona-2,4-diene depends on the mode of generating the cycloalkyne. Using diazomethylenecyclobutane and (bromocyclobutylidenemethyl)trimethylsilane as precursors affords cyclopentyne in an unencumbered form, whereas using dibromomethylenecyclobutane and 1,2-dibromocyclopentene yields a cyclopentyne-lithium bromide complex.

Original languageEnglish
Pages (from-to)1529-1534
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number5
DOIs
StatePublished - 5 Mar 1999

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