Communications

New type of a stable p-quinone methide possessing a pendant malonate moiety: synthesis and reactions with C-nucleophiles

Yu. A. Antonova, A. A. Tabolin

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia

Abstract: Cyclopropanation of 2,6-di-tert-butyl-4-vinylphenol with diazomalonates affords 4-hydroxyaryl-substituted cyclopropane dicarboxylates prone to easy ring opening into p-quinone methides tethered to malonate unit. The resulting quinone methides react with various C-nucleophiles to form the corresponding adducts thus serving as synthetic equivalents for donor-acceptor cyclopropanes in the homo-Michael addition. Side processes, namely, isomerization and dimerization of the quinone methides under basic conditions, were found.

Keywords: quinone methides, donor-acceptor cyclopropanes, cyclopropanation, ring opening, nitro compounds, diazo compounds, malonates.

Received: 10.02.2025
Accepted: 06.03.2025

Language: English

DOI: 10.71267/mencom.7746

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