B. Kopping, C. Chatgilialoglu, M. Zehnder
Jul 1, 1992
Citations
1
Influential Citations
123
Citations
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Journal
Journal of Organic Chemistry
Abstract
tris(trimethylsilyl)silane adds across the double bond of a variety of mono-, di-, and trisubstituted under free-radical conditions in good yields. The reaction, which proceeds via a free-radical chain mechanim, is highly regioselective (anti-Markovnikov). Addition to prochiral olefins bearing an ester group is highly stereoselective. The factors that control the stereochemistry have been discussed in term of preferred conformations of the intermediate carbon-centered radicals and are thought to be of steric origin