88415-65-0Relevant academic research and scientific papers
Unexpected cleavage of tetrahydrofuran by catalytic reductive lithiation
Streiff, Stephane,Ribeiro, Nigel,Desaubry, Laurent
, p. 346 - 347 (2004)
DBB, an electron transporter, can open THF at room temperature under sonication without any Lewis acid activation. This feature was successfully exploited in the straightforward synthesis of bis-silanes.
Synthesis of allylsilanes by reductive lithiation of thioethers
Streiff, Stephane,Ribeiro, Nigel,Desaubry, Laurent
, p. 7592 - 7598 (2007/10/03)
Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.
NEW TRANSFORMATIONS OF SUBSTITUED ALLENE SULPHOXIDES
Cutting, Ian,Parsons, Philip J.
, p. 4463 - 4464 (2007/10/02)
The preparation and reactions of trimethylsilyl substituted allene sulphoxides are described.Allenes (2) rearrange on warming to give α,β-unsaturated thiol esters.
