Diels-alder reactions with 2,2-bis (trifluoromethyl)-ethylene-1,1-dicarbonitrile as dienophile
In the cycloadditions of the title compound BTF to methylated and phenylated butadienes, NMR spectra of adducts allow to draw the demarcation line between [4+2] and [2+2] cycloadditions. 1-Substituted butadienes accept BTF in the direction less hindered by the bulky CF3groups. In rate comparison with TCNE, BTF shows electronic acceleration and steric deceleration.
Brueckner, Reinhard,Huisgen, Rolf
p. 3285 - 3288
(2007/10/02)
Substitutions and dehydrogenations by 2,2-bis(trifluoromethyl)-ethylene-1,1-dicarbonitrile via hydride abstraction
Substitution of benzylic H by the title compound (BTF) gives rise to products with -CH(CF3)2 terminus exclusively; an intermediate benzylic ion pair results from hydride transfer. Instead of ion recombination, proton transfer may be the concluding step generating dehydrogenation products and 2,2-bis(trifluoromethyl)ethane-1,1-dicarbonitrile.
Brueckner, Reinhard,Huisgen, Rolf
p. 1875 - 1878
(2007/10/02)
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