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
2,2-Bis(trifluoromethyl)ethylene-1,1-dicarbonitrile as a unique enophile
β Scribed by Huisgen, Rolf; Brueckner, Reinhard
- Book ID
- 127353240
- Publisher
- American Chemical Society
- Year
- 1991
- Tongue
- English
- Weight
- 351 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0022-3263
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π SIMILAR VOLUMES
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
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