Silylated cyclohexadienes as new radical chain reducing reagents: preparative and mechanistic aspects |
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Authors: | Studer Armido Amrein Stephan Schleth Florian Schulte Tobias Walton John C |
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Affiliation: | Fachbereich Chemie der Universit?t Marburg, Hans-Meerwein-Strasse, D-35032 Marburg. studer@mailer.uni-marburg.de |
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Abstract: | Various silylated 1,4-cyclohexadienes are presented as superior tin hydride substitutes for the conduction of various radical chain reductions. Debrominations, deiodinations, and deselenations can be performed using these environmentally benign reagents. Furthermore, Barton-McCombie-type deoxygenations using silylated cyclohexadienes are described. Radical cyclizations, ring expansions, and Giese-type addition reactions with the new tin hydride substitutes are presented. The polymerization of styrene can be regulated using silylated cyclohexadienes. Rate constants for hydrogen atom abstraction from two 1-silyl-cyclohexadienes by primary C-radicals were determined. The effects of the cyclohexadiene substituents on the reaction outcomes are discussed. Finally, qualitative EPR experiments on silyl radical expulsion from silylated cyclohexadienyl radicals are presented. |
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