82996-11-0

Upstream product

• 177-10-6 1,3-dioxolane-2-spirocyclohexane 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 

Relevant academic research and scientific papers

Selective synthesis of halosilanes from hydrosilanes and utilization for organic synthesis

Selective synthesis of halosilanes has been examined. Various types of halosilanes and halohydrosilanes, such as R3SiX, R2SiHX, R2SiX2, RSiH2X, RSiHX2 (X=Cl, Br, F), were obtained by the reactions of the corresponding hydrosilanes with Cu(II)-based reagents selectively in high yields. This method could be also applied to the synthesis of chlorofluorosilanes and chlorohydrogermanes. On the other hand, iodo- and bromosilanes and germanes were obtained by Pd- or Ni-catalyzed hydride-halogen exchange reactions of hydrosilanes with alkyl or allyl halides. Their synthetic applications have been demonstrated by using iodo- and bromosilanes and chlorofluorosilanes.

Ring-opening reactions of cyclic acetals and 1,3-oxazolidines with halosilane equivalents

Reactions of acetal and 1,3-oxazolidine rings were examined using two kinds of iodosilane equivalent reagents, a 1:2 mixture of Me3SiNEt2 and MeI (reagent 1a) and a 1:1 mixture of Et3SiH and MeI containing a catalytic amount of PdCl2 (reagent 1b). In the reactions of alkanone ethylene acetals with reagent 1a, a C-O bond in the acetal ring readily cleaved to give 2-(trimethylsiloxy)ethyl enol ethers. Similarly, the C-O bond of 1,3-oxazolidine rings cleaved to give ring-opened imine or enamine derivatives. The reactions of aromatic ketone ethylene acetals and cyclohexanone trimethylene acetal led to deprotection of the acetal unit to liberate free ketones. With reagent 1b, cycloalkanone ethylene acetal afforded a dimeric product with 2-iodoethyl alkenoate moieties, while aromatic ketone ethylene or trimethylene acetals produced deprotected ketones.

Ring-opening reactions of alkanone acetals with iodosilane equivalents for the formation of siloxyalkyl enol ethers

Reactions of ketone acetals with iodosilane equivalents were studied. Treatment of alkanone ethylene acetals with a 1:2 mixture of Et2NSiMe3 and MeI afforded 2-siloxyethyl enol ethers in good yield. Benzophenone ethylene acetal underwent deprotection with the iodosilane equivalents, giving benzophenone.

Synthesis of Cyclic and Acyclic Enol Ethers (Vinyl Ethers)

A general method has been developed for the conversion of both cyclic and acyclic acetals of cyclic ketones, acyclic ketones, and aldehydes into enol ethers through treatment of the acetal with trimethylsilyl triflate in the presence of N,N-diisopropylethylamine.The range of isolated yields of enol ethers from the various classes of acetals was as follows: cyclic acetals of cyclic ketones, 83-98percent; acyclic acetals of ketones, 72-94percent; acyclic and cyclic acetals of aldehydes, 65-90percent.

General Method for the Synthesis of Enol Ethers (Vinyl Ethers) from Acetals

A general, high yield method for the synthesis of enol ethers from acetals has been devised that involves treatment of an appropriate acetal with a 10-75percent molar excess of trimethylsilyl triflate and a 20-90percent molar excess of N,N-diisopropylethy