Aromaticity of the Bergman, Myers-Saito, Schmittel, and directly related cyclizations of enediynes - Research portal of Justus Liebig University Giessen:

Journal article

Aromaticity of the Bergman, Myers-Saito, Schmittel, and directly related cyclizations of enediynes

Authors list: Stahl, F; Moran, D; von Ragué, Schleyer; Prall, M; Schreiner, PR

Publication year: 2002

Pages: 1453-1461

Journal: The Journal of Organic Chemistry

Volume number: 67

Issue number: 5

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/jo015728s

Publisher: American Chemical Society

Abstract:
Aromaticity criteria (magnetic susceptibility exaltations, nucleus independent chemical shifts (NICS), and aromatic stabilization energy (ASE) evaluations) for enediyne and enyne-allene cyclizations evaluated at (UBS)-BLYP/6-31G* all agree that the degrees of cyclic electron delocalization of the benzenoid systems formed by the Bergman (3) and Myers-Saito reactions (5) are comparable to benzene. The reaction enthalpy differences between the parent cyclizations and their benzannelated analogues are not entirely due to disparities in gained ASE during the reactions. The alternative formation of fulvene biradicals is not accompanied by favorable aromatic effects.

Authors/Editors

- Uni.-Prof. Dr. Peter Richard Schreiner, PhD

Citation Styles

Harvard Citation style: Stahl, F., Moran, D., von Ragué, S., Prall, M. and Schreiner, P. (2002) Aromaticity of the Bergman, Myers-Saito, Schmittel, and directly related cyclizations of enediynes, The Journal of Organic Chemistry, 67(5), pp. 1453-1461. https://doi.org/10.1021/jo015728s

APA Citation style: Stahl, F., Moran, D., von Ragué, S., Prall, M., & Schreiner, P. (2002). Aromaticity of the Bergman, Myers-Saito, Schmittel, and directly related cyclizations of enediynes. The Journal of Organic Chemistry. 67(5), 1453-1461. https://doi.org/10.1021/jo015728s