42150-16-3Relevant articles and documents
An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source
Rodygin, Konstantin S.,Ananikov, Valentine P.
, p. 482 - 486 (2016)
Chemical reactions involving high-pressure acetylene are not easily performed in a standard laboratory setup. The risk of explosion and technical difficulties drastically complicate the equipment and greatly increase the cost. In this study, we propose th
Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron-rich alkenes
Bauld, Nathan L.,Aplin, J. Todd,Yueh, Wang,Endo, Stephanie,Loving, Angie
, p. 15 - 24 (2007/10/03)
Both experimental and theoretical studies confirm that the formation of aryl vinyl ether and aryl vinyl sulfide cation radicals from the corresponding neutral substrates correlates with the Brown σ+ parameters as opposed to Hammett σ values. Peak oxidation potentials for both classes of substrates correlate preferentially with σ+, as do gas-phase ionization energies calculated by both semi-empirical and ab initio methods. In contrast, the protonation energies of the same substrates, which relate to carbocation formation, correlate preferentially with σ values, as do rates of protonation and other electrophilic additions. These observations permit a sharp distinction between electrophilic and electron transfer reactions of these two common classes of electron-rich substrates. Using this criterion, the cycloadditions of tetracyanoethylene to these substrates are found to proceed via an electrophilic mechanism, rather than by a previously proposed electron transfer mechanism.
