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

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

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2025, Volume: 35, Number: 5, Pages: 533-536 Pages count : 4 DOI: 10.71267/mencom.7746

Authors

Antonova Yulia A. ¹ , Tabolin Andrey Aleksandrovich ¹

Affiliations

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

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.

Antonova Y.A. , Tabolin A.A.
New type of a stable p-quinone methide possessing a pendant malonate moiety: synthesis and reactions with C-nucleophiles
Mendeleev Communications. 2025. V.35. N5. P.533-536. DOI: 10.71267/mencom.7746 WOS Scopus OpenAlex

≡ Web of science:	WOS:001544036400010
≡ Scopus:	2-s2.0-105011984123
≡ OpenAlex:	W4413064858