Keywords
cyclopropanation
diazo compounds
donor-acceptor cyclopropanes
malonates.
nitro compounds
quinone methides
ring opening
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.
Funders
Russian Science Foundation
25-23-00582
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