Reactivity umpolung of the cycloheptatriene core in hexa(methoxycarbonyl)cycloheptatriene

• Dmitry N. Platonov,
• Alexander Yu. Belyy,
• Rinat F. Salikov,
• Kirill S. Erokhin and
• Yury V. Tomilov

Beilstein J. Org. Chem. 2026, 22, 64–70, doi:10.3762/bjoc.22.2

• , include the formation of norcaradienes, dihydroindazoles, a tetracyclodecene and a hydrazonocycloheptatriene derivative. Keywords: azo shift; cascade reactions; cycloheptatriene; relief of antiaromaticity; umpolung; Introduction Reactivity umpolung [1] is a synthetic concept in organic chemistry that

• , the antiaromatic properties of anion 2 [21] allow to regard these reactions as one of those driven by the relief of antiaromaticity [22][23][24][25][26][27]. Results and Discussion In our previous work [21], we demonstrated that most cycloheptatrienyl anions prefer conformers distorted to an allylic

• conditions and selectivity revealed different controls in the cases of alkylation and halogenation reactions. Additionally, the reactions can be distinguished as driven by the relief of antiaromaticity. The expected and the unexpected in selected synthetic strategies. Distortion in antiaromatic hepta- and