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

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

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2026, Volume: 22, Pages: 64-70 Pages count : 7 DOI: 10.3762/bjoc.22.2

Authors

Platonov Dmitry N ¹ , Belyy Alexander Yu ¹ , Salikov Rinat F ^2,1 , Erokhin Kirill S ¹ , Tomilov Yury V ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	Higher School of Economics National Research University, 101000 Moscow, Russian Federation

Funding (1)

N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences

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.

Platonov D.N. , Belyy A.Y. , Salikov R.F. , Erokhin K.S. , Tomilov Y.V.
Reactivity umpolung of the cycloheptatriene core in hexa(methoxycarbonyl)cycloheptatriene
Beilstein Journal of Organic Chemistry. 2026. V.22. P.64-70. DOI: 10.3762/bjoc.22.2 OpenAlex

OpenAlex:

W7118173485

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