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

Frank Stahl, Damian Moran, Paul Von Ragué Schleyer, Matthias Prall, Peter R. Schreiner*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

76 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1453-1461
Number of pages9
JournalJournal of Organic Chemistry
Volume67
Issue number5
DOIs
Publication statusPublished - 8 Mar 2002
Externally publishedYes

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