68669-67-0

Basic information

• Product Name: (Z)-trimethyl(2-phenylprop-1-en-1-yl)silane
• Synonyms: (Z)-trimethyl(2-phenylprop-1-en-1-yl)silane
• CAS NO: 68669-67-0
• Molecular Weight: 190.36
• Mol File: 68669-67-0.mol

Chemical Properties

• CAS DataBase Reference: (Z)-trimethyl(2-phenylprop-1-en-1-yl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-trimethyl(2-phenylprop-1-en-1-yl)silane(68669-67-0)
• EPA Substance Registry System: (Z)-trimethyl(2-phenylprop-1-en-1-yl)silane(68669-67-0)

Safety Data

• Hazardous Substances Data: 68669-67-0(Hazardous Substances Data)

Upstream product

• 2612-42-2 (dibromomethyl)trimethylsilane 
• 98-86-2 acetophenone 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 68669-68-1 (3E)-4-phenyl-1-trimethylsilyl-3-penten-1-yne 
• 98-83-9 isopropenylbenzene 
• 97607-44-8 1-trimethylsilyl-2-phenyl-2-trimethylstannyl-ethene 
• 77-78-1 dimethyl sulfate 
• 130837-36-4 (E)/(Z)-2-methyl-2-phenyl-1-trimethylsilyl-1-trimethylstannylethene 

Relevant articles and documents

Chromium-catalyzed arylmagnesiation of alkynes

Equation presented Arylmagnesiation of unfunctionalized alkynes in the presence of catalytic amounts of chromium(II) chloride and pivalic acid proceeds with high stereoselectivity. The alkenylmagnesium intermediate reacts with various electrophiles to afford the corresponding tetrasubstituted olefins in good yields.

Geometric E→Z Isomerisation of Alkenyl Silanes by Selective Energy Transfer Catalysis: Stereodivergent Synthesis of Triarylethylenes via a Formal anti-Metallometallation

An efficient geometrical E→Z isomerisation of alkenyl silanes is disclosed via selective energy transfer using an inexpensive organic sensitiser. Characterised by operational simplicity, short reaction times (2 h), and broad substrate tolerance, the reaction displays high selectivity for trisubstituted systems (Z/E up to 95:5). In contrast to thermal activation, directionality results from deconjugation of the π-system in the Z-isomer due to A1,3-strain thereby inhibiting re-activation. The structural importance of the β-substituent logically prompted an investigation of mixed bis-nucleophiles (Si, Sn, B). These versatile linchpins also undergo facile isomerisation, thereby enabling a formal anti-metallometallation. Mechanistic interrogation, supported by a theoretical investigation, is disclosed together with application of the products to the stereospecific synthesis of biologically relevant target structures.

Alkylidenation of carbonyl compounds with gem-dizincioalkanes mediated with titanium dichloride

Olefination of carbonyl compounds with gem-dizincio-alkanes, bis(iodozincio)methane, 1,1-bis(iodozincio)ethane, and bis(bromozincio)methyltrimethylsilane, afforded the corresponding olefins in good to excellent yields.

STUDIES ON THE SYNTHETIC USE OF STEREODEFINED OLEFINS WITH GEMINAL TRIMETHYLSILYL AND TRIMETHYLSTANNYL SUBSTITUENTS

The synthetic use of 2-alkyl and 2-(hetero)aryl substituted (Z)- and (E)-1-trimethylsilyl-1-trimethylstannylethenes of general formula (Z)-2, (E)-2, (Z)-3 and (E)-3, via the corresponding 1-silylethenyllithiums prepared by tin-lithium exchange reactions a

STEREOSELECTIVE SYNTHESIS AND CHARACTERIZATION OF 2-ALKYL AND 2-(HETERO)ARYL SUBSTITUTED (Z)- AND (E)-1-TRIMETHYLSILYL-1-TRIMETHYLSTANNYLETHENES

The regio- and stereoselective syntheses of the (Z)- and (E)-stereoisomers of some 1-trimethylsilyl-2-(hetero)arylethenylstannanes and 1-trimethylsilyl-2-alkylethenyltrimethylstannanes of general formula (Z)-2, (E)-2, (Z)-3, and (E)-3, respectively, are reported.The strategy followed to prepare (Z)-2, (E)-2, and (E)-3, involves: a) stereoselective cis- and trans-hydroalumination of the corresponding 1-alkynylsilanes; b) conversion of the stereodefined 1-alkenyl-1-silylalanes so obtained into the corresponding aluminates; and c) the cuprous iodide-triethyl phosphite complex mediated reaction of these aluminates with trimethyltin chloride.Compounds (Z)-3, have been prepared by carbocupration of ethynyltrimethylsilane, 12, followed by treatment with trimethyltin chloride.Compounds (Z)-2, (E)-2, (Z)-3, and (E)-3, have been characterized by MS spectrometry and 1H NMR spectroscopy and their configuration has been unambiguously assigned by 119Sn NMR spectroscopy.The results of an attempt to syntesize a 2-alkyl substituted (E)-1-trimethylsilyl-1-trimethylstannyl-2-arylethene are also discussed.

Formation and Reactions of Olefins with Vicinal Silyl and Stannyl Substituents

The silicon-tin bond in Me3SiSnR3 (R=Me, n-Bu) adds regio- and stereospecifically to 1-alkynes and also to a limited number of nonterminal alkynes when Pd(PPh3)4 is added as a catalyst.The use of the (Z)-silylstannylalkenes thus formed in synthesis either