The interaction of the title compound (BTF) with unsaturated nucleophiles (ketene dithioacetals, a-substituted vinyl ethers, N-vinylcarboxamides, enols, furans, N-methylpyrrole, N-methylindole) effects substitution of vinylic or aromatic H by -C(CF3)2-CH(CN)2. The highly electrophilic 2,2-bis(trifl
Substitutions and dehydrogenations by 2,2-bis(trifluoromethyl)-ethylene-1,1-dicarbonitrile via hydride abstraction
✍ Scribed by Reinhard Brückner; Rolf Huisgen
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 291 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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(triiuoromethyl)ethane-l , 1 -dicarbonitrile.
📜 SIMILAR VOLUMES
The effects of substituents and solvent variation on the rate constants are in harmony with a concerted cycloaddition. In the preceding communication we described reactions of 2,2-bis(trifluoromethyl)ethylene-1 ,I-dicarbonitrile (BTF; 1) with styrenes 2 2. By rapid reversible Diels-Alder additions w