503299-91-0Relevant academic research and scientific papers
Silylated cyclohexadienes as new radical chain reducing reagents: Preparative and mechanistic aspects
Studer, Armido,Amrein, Stephan,Schleth, Florian,Schulte, Tobias,Walton, John C.
, p. 5726 - 5733 (2003)
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 Giesetype 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.
Silylated cyclohexadienes in radical chain hydrosilylations
Amrein, Stephan,Studer, Armido
, p. 3559 - 3574 (2007/10/03)
A new method for the mild radical hydrosilylation of alkenes and alkynes is described. Silylated cyclohexadienes that can be readily prepared on large scale are used as radical hydrosilylating reagents. Nonactivated alkenes and alkynes are hydrosilylated in high yields. The reaction can be combined with C-C bond formation, as demonstrated for the preparation of silylated cycloalkanes from the corresponding dienes. Furthermore, radical hydrosilylations in combination with β-fragmentation reactions for the synthesis of allylsilanes and hydrosilylations of aldehydes and ketones providing protected alcohols can be readily performed by this strategy.
Radical transfer hydrosilylation/cyclization using silylated cyclohexadienes
Amrein, Stephan,Timmermann, Andreas,Studer, Armido
, p. 2357 - 2360 (2007/10/03)
(matrix presented) A new method for mild metal-free hydrosilylation is described. Silylated cyclohexadienes are used as radical transfer hydrosilylating reagents for various double and triple bonds. A trialkylsilane is transferred from a cyclohexadiene mo
