31930-43-5

Basic information

• Product Name: Silane, triethyl-1-octenyl-, (E)-
• CAS NO: 31930-43-5
• Molecular Formula: C14H30Si
• Molecular Weight: 226.478
• Mol File: 31930-43-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Silane, triethyl-1-octenyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, triethyl-1-octenyl-, (E)-(31930-43-5)
• EPA Substance Registry System: Silane, triethyl-1-octenyl-, (E)-(31930-43-5)

Safety Data

• Hazardous Substances Data: 31930-43-5(Hazardous Substances Data)

Upstream product

• 617-86-7 triethylsilane 
• 629-05-0 n-octyne 
• 111-66-0 oct-1-ene 

Relevant articles and documents

Hydrosilylation of Terminal Alkynes Catalyzed by a ONO-Pincer Iridium(III) Hydride Compound: Mechanistic Insights into the Hydrosilylation and Dehydrogenative Silylation Catalysis

The catalytic activity in the hydrosilylation of terminal alkynes by the unsaturated hydrido iridium(III) compound [IrH(κ3-hqca)(coe)] (1), which contains the rigid asymmetrical dianionic ONO pincer ligand 8-oxidoquinoline-2-carboxylate, has been studied. A range of aliphatic and aromatic 1-alkynes has been efficiently reduced using various hydrosilanes. Hydrosilylation of the linear 1-alkynes hex-1-yne and oct-1-yne gives a good selectivity toward the β-(Z)-vinylsilane product, while for the bulkier t-Bu-C≡CH a reverse selectivity toward the β-(E)-vinylsilane and significant amounts of alkene, from a competitive dehydrogenative silylation, has been observed. Compound 1, unreactive toward silanes, reacts with a range of terminal alkynes RC≡CH, affording the unsaturated η1-alkenyl complexes [Ir(κ3-hqca)(E-CH=CHR)(coe)] in good yield. These species are able to coordinate monodentate neutral ligands such as PPh3 and pyridine, or CO in a reversible way, to yield octahedral derivatives. Further mechanistic aspects of the hydrosilylation process have been studied by DFT calculations. The catalytic cycle passes through Ir(III) species with an iridacyclopropene (η2-vinylsilane) complex as the key intermediate. It has been found that this species may lead both to the dehydrogenative silylation products, via a β-elimination process, and to a hydrosilylation cycle. The β-elimination path has a higher activation energy than hydrosilylation. On the other hand, the selectivity to the vinylsilane hydrosilylation products can be accounted for by the different activation energies involved in the attack of a silane molecule at two different faces of the iridacyclopropene ring to give η1-vinylsilane complexes with either an E or Z configuration. Finally, proton transfer from a η2-silane to a η1-vinylsilane ligand results in the formation of the corresponding β-(Z)- and β-(E)-vinylsilane isomers, respectively.