4 research outputs found
Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel–Crafts Electrophilic Substitution
The acid-catalyzed cyclization
of a wide range of triaryl-substituted divinyl ketones has been studied.
It was found that the reaction pathway strongly depends on the nature
of the aryl substituent at the α-position to the carbonyl group.
An electron-rich aromatic substituent promotes the reaction to proceed
through the intramolecular Friedel–Crafts electrophilic substitution
giving dihydroÂnaphthalene derivatives. In contrast, the presence
of an electron-deficient substituent is favorable for the Nazarov
4Ď€-conrotatory cyclization yielding triaryl-substituted cyclopentenones.
The electrophilic substitution reaction was applied to thiophene and
thiazole derivatives
Triaryl-Substituted Divinyl Ketones Cyclization: Nazarov Reaction versus Friedel–Crafts Electrophilic Substitution
The acid-catalyzed cyclization
of a wide range of triaryl-substituted divinyl ketones has been studied.
It was found that the reaction pathway strongly depends on the nature
of the aryl substituent at the α-position to the carbonyl group.
An electron-rich aromatic substituent promotes the reaction to proceed
through the intramolecular Friedel–Crafts electrophilic substitution
giving dihydroÂnaphthalene derivatives. In contrast, the presence
of an electron-deficient substituent is favorable for the Nazarov
4Ď€-conrotatory cyclization yielding triaryl-substituted cyclopentenones.
The electrophilic substitution reaction was applied to thiophene and
thiazole derivatives