Journalartikel

Jahr der Veröffentlichung: 2002

Seiten: 1453-1461

Zeitschrift: The Journal of Organic Chemistry

Bandnummer: 67

Heftnummer: 5

ISSN: 0022-3263

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

Verlag: 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.

Harvard-Zitierstil: 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-Zitierstil: 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