Synthesis of 2-(4,5-Dihydrofuryl)- and 2-(Tetrahydrofuryl)dimethylhydrosilanes. Rearrangement of 2-(Tetrahydrofuryl)dimethylhydrosilane with Ring Expansion

Syntheses, Characterization, and Reactivity of Diruthenium Hydrido Complexes

“…The rearrangement of 2-(dimethylsilyl)tetrahydrofuran to the corresponding oxasilacyclohexane product has been previously reported by Lukevics and co-workers. 15,16 In their study, the authors report that the rearrangement reaction is catalyzed by Pd/Al 2 O 3 (eq 6), and a labeling experiment confirmed that the Si−H/D bond was being cleaved in order for the rearrangement to occur.…”

Generation and reactivity of α-metalated vinyl ethers

“…Some of the silylated derivatives such as 300d are novel hydrosilylation reagents. 265,267 The utility of Li-DHF and Li-DHP as cyclic acyl anion equivalents is readily apparent from Scheme 84. The carbinol 291 and alkylated products 299 and 300 are easily transformed into synthetically useful compounds, including substituted alkenes, spiroketals and keto acids or alcohols.…”

-Heteroatom-Substituted 1-Alkenyllithium Reagents: Carbanions and Carbenoids for C–C Bond Formation

“…[32] tert-Butyllithium in tetrahydrofuran [33] or tetrahydropyran [34] as well as a mixture of potassium tert-butoxide and butyllithium are also suitable for deprotonating alkyl alkenyl ethers. A series of a-lithiated vinyl ethersÐsuch as 2-lithio-4,5-dihydrofuran (17), [32,36,37] 2-lithio-5,6-dihydropyran (18), [32,38] and 2-litho-5,6-dihydro-1,4-dioxin (19) [39,40] Ðas well as the metalated carbamide 20 [41] are available with this or a similar procedure. The metalated vinyl ethers are much more stable than the 1-halo-1-lithioalkenes; the lithiated dioxin 19 can supposedly be kept in solution at 20 8C for several days.…”