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

Beilstein Journal of Organic Chemistry 2026 Open access

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Authors: Dmitry Nikolaevich Platonov, Alexander Yu Belyy, Rinat Faritovich Salikov, Kirill Sergeevich Erokhin, Yury Vasil'evich Tomilov
DOI: 10.3762/bjoc.22.2
Cited by: 1
References: 38

Abstract

A reactivity umpolung approach for the derivatization of cycloheptatrienes was extended to hexa(methoxycarbonyl)cycloheptatriene, which forms the corresponding anion reactive towards electrophiles. Despite the presence of four potential reactive sites, the reactions mainly involve the initial electrophilic attack onto the α-position relative to the hydrogen atom. The selectivity is either due to the high stability of the α-nucleophilic conformer or due to the promotion by the adjacent ester group. Cascade reactions upon the target connection, if installed, include the formation of norcaradienes, dihydroindazoles, a tetracyclodecene and a hydrazonocycloheptatriene derivative.

Fields of Study & Subjects

Synthesis and Properties of Aromatic Compounds Coordination Chemistry and Organometallics Chemical Reactions and Mechanisms

Publication details

Journal / source
Beilstein Journal of Organic Chemistry
Publisher
Beilstein Institut
Volume
22
Pages
64–70
Publication date
5 January 2026
Language
EN