130178-38-0Relevant articles and documents
Kinetics of [2 + 2] cycloadditions of 2,2-bis(trifluoromethyl)ethylene-1,1- dicarbonitrile with enol ethers, 1,1-dimethylbutadiene, and allytrimethylsilane
Bruckner,Huisgen
, p. 2557 - 2560 (1990)
The rate constant with ethyl vinyl ether is enhanced by α-donor substituents whereas β-methyl groups strongly retard by steric hindrance. The title compound (BTF) is 2400 times more active than TCNE towards ethyl vinyl ether in benzene. The rates of the title reactions increase 70- to 2300-fold with solvent polarity.
[2 + 2] cycloadditions of 2,2-bis(trifluoromethyl)ethylene-1,1-dicarbonitrile with enol ethers, 1,1-dimethylbutadiene, and allyltrimethylsilane
Huisgen,Bruckner
, p. 2553 - 2556 (1990)
Vinyl ethers and the title compound (BTF) form cyclobutanes via 1,4-dipoles which can be intercepted with ethanol or acetic acid. Cis- and trans-1-ethoxypropene react with BTF nonstereospecifically in agreement with a stepwise mechanism. 1,1-Dimethylbutadiene or allytrimethylsilane undergo [2 + 2] cycloadditions with BTF, too.