Biradical and zwitterionic cyclizations of oxy-substituted enyne-allenes

Christopher J. Cramer, Bethany L. Kormos, Mark Seierstad, Edward C. Sherer, Paul Winget

Research output: Contribution to journalArticlepeer-review

25 Scopus citations


(formula presented) Oxyanion substitution of enyne-allenes causes both Myers-Saito and Schmittel cyclizations to switch their product formation preferences from diradicals to polar, closed-shell singlets. The oxyanion stabilization is larger for the Schmittel products than the Myers-Saito products because the latter must sacrifice aromaticity to maximize interaction. The changing character of the different reaction paths is reflected in their activation energies.

Original languageEnglish (US)
Pages (from-to)1881-1883
Number of pages3
JournalOrganic Letters
Issue number12
StatePublished - Jun 14 2001


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