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2,2-Bis(trifluoromethyl)ethylene-1,1-dicarbonitrile as a unique enophile

✍ 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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πŸ“œ SIMILAR VOLUMES


Electrophilic substitutions by 2,2-bis(t
✍ Reinhard BrΓΌckner; Rolf Huisgen πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 French βš– 270 KB

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,
✍ Reinhard BrΓΌckner; Rolf Huisgen πŸ“‚ Article πŸ“… 1991 πŸ› Elsevier Science 🌐 French βš– 291 KB

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

2,2-bis(trifluoromethyl)ethylene-1,1-dic
✍ Reinhard BrΓΌckner; Rolf Huisgen πŸ“‚ Article πŸ“… 1990 πŸ› Elsevier Science 🌐 French βš– 265 KB

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