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DEHYDROBENZENE IN THE REACTION OF A TANDEM [4+2]/[4+2] CYCLOADDITION WITH LINEAR BIS-FURYLDIENES

Elizaveta A. Kvyatkovskaya, Polina P. Epifanova, Kseniya K. Borisova, Sophia I. Borovkova, Mikhail S. Grigoriev, Fedor I. Zubkov
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Abstract


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.


Keywords


aryne; dehydrobenzene; 1,4:5,8-diepoxynaphthalenes; furan; 7-oxabicyclo[2.2.1]heptane; IMDAF reaction; intramolecular Diels–Alder reaction; tandem [4+2]/[4+2] cycloaddition.

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