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Biradical and Zwitterionic Cyclizations of Oxy-substituted Enyne-Allenes

Cramer, C. J.; Kormos, B. L.; Seierstad, M.; Sherer, E. C.; Winget, P.
Org. Lett. 2001, 3, 1881.

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.

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