4235-65-8

Upstream product

• 591-50-4 iodobenzene 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 4098-98-0 tetrakis(trimethylsilyl)silane 
• 75-77-4 chloro-trimethyl-silane 
• 98-13-5 Phenyltrichlorosilane 
• 5565-32-2 chlorotris(trimethylsilyl)silane 

Downstream Products

• 72169-01-8 9syn-phenyl-9anti-trimethylsilanyl-9-sila-bicyclo[4.2.1]non-7-ene 
• 72169-02-9 9anti-phenyl-9syn-trimethylsilanyl-9-sila-bicyclo[4.2.1]non-7-ene 
• 78227-47-1 1-acetoxy-1-phenyl-1-vinyltrimethyldisilane 
• 72169-09-6 1-(1-methylallyl)-1-phenyl-2,2,2-trimethyldisilane 
• 78227-41-5 1-ethoxy-1-phenyl-1-vinyltrimethyldisilane 
• 78227-38-0 1-chloro-1-phenyl-1-vinyltrimethyldisilane 
• 64-17-5 ethanol 
• 78227-40-4 1-methoxy-1-phenyl-1-vinyltrimethyldisilane 
• 78227-50-6 1-phenyl-1-trimethylsilyl-2-ethoxy-1-silacyclopropane 
• 78227-42-6 1-chloro-1-(1'-ethoxyethyl)-1-phenyltrimethyldisilane 
• 78227-43-7 1-chloro-1-(2'-ethoxyethyl)-1-phenyltrimethyldisilane 
• 63242-89-7 2-(1'-methoxy-1'-phenyltrimethyldisilanyl)-1-hexene 

Relevant academic research and scientific papers

Novel one-pot synthesis of aryltris(trimethylsilyl)silanes

The simple combination of tris(trimethylsilyl)-potassium, ArMgBr, and ArBr provides a novel one-pot synthesis of aryl(tristrimethylsilyl)silanes. A mechanistic rationale for this conversion is proposed.

Tris(trimethylsilyl)silylboronate Esters: Novel Bulky, Air- and Moisture-Stable Silylboronate Ester Reagents for Boryl Substitution and Silaboration Reactions

New, bulky tris(trimethylsilyl)silylboronate pinacol and hexylene glycol esters ((TMS)3Si-B(pin) and (TMS)3Si-B(hg)) were prepared in 46 and 61% yields, respectively, by the reaction of tris(trimethylsilyl)silylpotassium with the corresponding boron electrophiles. Notably, these silylboronate esters exhibited high stability to air and silica gel and were applied to the transition-metal-free boryl substitution of aryl halides, providing the desired borylated products in high yields with excellent B:Si ratios (up to 96% yield, B/Si = 99/1). These new silylboronate esters were also applied to a sequential borylation/cross-coupling process with various aryl halides, as well as the base-mediated silaboration of styrene.

Preparation of oligosilanes containing perhalogenated silyl groups (-SiX3, -SiX2-, >SiX-, X = Cl, Br) and their hydrogenation by stannanes

Starting from methylphenylsubstituted oligosilanes the disilanes SiX3-SiXi,Me3-i (i = 0, 1, 2; X = Cl, Br), trisilanes SiX2(SiXiMe3-i) (i = 0, 1) and branched tetrasilanes SiX(SiXMe2)3 were synthesized and their behavior towards the Lewis-base catalyzed hydrogenation by stannanes was investigated. In the case of methylchlorodisilanes SiCl3-SiCliMe3-i Si-Si bond cleavage competes with the hydrogenation reaction.

Photoelectron spectra and molecular properties. CXXXVIII. 1,4-Dibenzene: synthesis, structural analogy, photoelectron spectrum and ESR/ENDOR cheracterization of its radical anion

1,4-Dibenzene 3SiC6H4Si3, which contains eight silicon centers, has been synthesized and some of its molecular properties determined.For a single crystal structure determination, its isovalence-electronic and sterically more crowded carbon analogue, 3CC6H4C3, was selected.It shows van der Waals interactions due ro close lattice packing.Despite its shorther SiC bonds, however, no severe skeletal distortions due to overcrowding are observed; the contraction of the benzene ipso angles to 114 deg is due to the donor effect of the tris(trimethylsilyl)methyl substituents.The first vertical ionization energy of the title molecule, IEv1 = 7.37 eV, is the lowest of all of these recorded up to now for 1,4-dialkyl or 1,4-disilyl substituted benzene derivatives; for the monosubstituted tris(trimethylsilyl)silyl derivative 3SiC6H5 the value is 8.04 eV.Cyclovoltammetric experiments in aprotic solution reveal a velocity-dependent irreversible oxidation above + 1.28 eV and no electron insertion within the measurement range to -2.9 eV.The reduction to the radical anion, however, can be achieved in THF solution containing cryptand at a potassium metal mirror.According to the spin populations deduced from 1H and 29Si ENDOR signal patterns, more than half of the spin is located in the two 3Si groups.Results of molecular orbital (MO) calculations and comparison with equivalent molecular states of chemically related compounds allow rationalization of the effects of the 3Si substituent, which acts as a strong electron doenor in radical cations and as a strong electron acceptor in radical anions.

Reaction of phenyl(trimethylsilyl)silylene with chloromethanes; Insertion into C-Cl bond and abstraction of chlorine and HCl

Photolysis of tris(trimethylsilyl)phenylsilane in chloromethanes, ClnCX(4-n), (n = 1-4, X = H, alkyl, and Cl) produced phenyl(trimethylsilyl)silylene as a major intermediate, which afforded three types of products: 1,1-dichloro-1-phenyltrimethyldisilane via abstraction of two chlorine atoms, 1-alkyl-1-chloro-1-phenyltrimethyl-disilane via insertion into the C-Cl bond, and 1-chloro-1-phenyl-2,2,2-trimethyldisilane via abstraction of HCl.Possible reaction mechanisms for the formation of these products were discussed based on initial formation of an 1,2-zwitterionic intermediate.A small amount of a radical-reaction product, 2-chloro-2-phenyl-hexamethyltrisilane, and a product considered to be a cyclohexadienyl derivative were detected in all cases as minor products.