Dehydrobenzene in the Reaction of a Tandem [4+2]/[4+2] Cycloaddition with Linear bis-furyldienes

Tandem [4+2]/[4+2] cycloaddition between bis-dienes containing two furan rings and dehydrobenzene as a dienophile was studied. It was shown that dehydrobenzene generated in situ from 2-(trimethylsilyl)phenyl trifluoromethanesulfonate is capable of a facile intermolecular [4+2] cycloaddition to a fur...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2021-09, Vol.57 (9), p.949-961
Main Authors: Kvyatkovskaya, Elizaveta A., Epifanova, Polina P., Borisova, Kseniya K., Borovkova, Sophia I., Grigoriev, Mikhail S., Zubkov, Fedor I.
Format: Article
Language:English
Subjects:
Adducts
Chemistry
Chemistry and Materials Science
Cycloaddition
Diels-Alder reaction
Diels-Alder reactions
Dienes
Furans
High temperature
Organic Chemistry
Pharmacy
Room temperature
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Summary:Tandem [4+2]/[4+2] cycloaddition between bis-dienes containing two furan rings and dehydrobenzene as a dienophile was studied. It was shown that dehydrobenzene generated in situ from 2-(trimethylsilyl)phenyl trifluoromethanesulfonate is capable of a facile intermolecular [4+2] cycloaddition to a furan moiety of a diene at room temperature. The next step, that involves intramolecular Diels–Alder reaction (the IMDAF reaction) with the second furan ring, requires elevated temperature up to 80°С. It has been shown that even under optimal conditions the yields of the target annulated 1,4:5,8-diepoxynaphthalenes do not exceed 50%. The main byproducts are double cycloaddition adducts formed during the interaction of two aryne subunits with both furan rings of the initial bis-diene.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-021-03005-2