Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control†
Kseniya K.
Borisova, 
a
Eugeniya V.
Nikitina,
a
Roman A.
Novikov,
b
Victor N.
Khrustalev,
a
Pavel V.
Dorovatovskii,
c
Yan V.
Zubavichus,
c
Maxim L.
Kuznetsov,
d
Vladimir P.
Zaytsev,
a
Alexey V.
Varlamov
a
and
Fedor I.
Zubkov
*a
a
Eugeniya V.
Nikitina,
a
Roman A.
Novikov,
b
Victor N.
Khrustalev,
a
Pavel V.
Dorovatovskii,
c
Yan V.
Zubavichus,
c
Maxim L.
Kuznetsov,
d
Vladimir P.
Zaytsev,
a
Alexey V.
Varlamov
a
and
Fedor I.
Zubkov
*a
Abstract
The tandem [4+2] cycloaddition between hexafluoro-2-butyne and bis-furyl dienes, like difurfuryl ester, at room temperature leads to the kinetically controlled “pincer”-adducts – annulated 4a,8a-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes. On the other hand, if these reactions proceed at 140 °C, only the thermodynamically controlled “domino”-adducts – annulated 2,3-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes – are formed. Therefore, a very rare and unexpected example of full kinetic and thermodynamic control in the Diels–Alder reaction is reported in this paper.
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