Biradical and zwitterionic cyclizations of oxy-substituted enyne-allenes

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

doi:10.1021/ol015935e

Biradical and zwitterionic cyclizations of oxy-substituted enyne-allenes

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

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Abstract

(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 language	English (US)
Pages (from-to)	1881-1883
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	12
DOIs	https://doi.org/10.1021/ol015935e
State	Published - Jun 14 2001

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title = "Biradical and zwitterionic cyclizations of oxy-substituted enyne-allenes",

abstract = "(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.",

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T1 - Biradical and zwitterionic cyclizations of oxy-substituted enyne-allenes

AU - Cramer, Christopher J.

AU - Kormos, Bethany L.

AU - Seierstad, Mark

AU - Sherer, Edward C.

AU - Winget, Paul

PY - 2001/6/14

Y1 - 2001/6/14

N2 - (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.

AB - (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.

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Biradical and zwitterionic cyclizations of oxy-substituted enyne-allenes

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