20107-37-3Relevant academic research and scientific papers
Reaktionen Methyl- und Trimethylsubstituierter Vinylsilane- bzw. -Disilane mit LiBut
Auner, N.
, p. 59 - 82 (1987)
The reactions of the vinylsilanes Me3SiVi, Me2SiVi2, Me3SiSiMe2Vi, (Me2ViSi)2 and (Me3Si)3SiVi with LiBut in n-pentane in the first step lead to α-lithioalkylsilanes of different stabilities.The secondary reactions are clearly controlled by the reaction conditions: in dilute solution the intramolecular 2,3-LiH elimination to trans-ethene derivatives R3SiCH=CHBut is dominating, and at higher concentrations intermolecular coupling reactions of the Li-alkylsilanes with further vinylsilanes occur, with elimination of LiH and formation of olefinic compounds.At higher temperatures and owing to separation processes, competitive reactions result in the formation of isobutyl derivatives, the elimination of isobutane and the cleavage of Si-Vi bonds.In spite of the complicated reaction mixture a clear interpretation of the results is presented.
TRANS ALKENES AND VINYLSILANES FROM TRANS-α-STANNYL EPOXIDES
Soderquist, John A.,Lopez, Carlos
, p. 6305 - 6306 (1991)
The reaction of trans-α-epoxystannanes (1) with an excess of alkyllithium reagents was found to undergo reductive alkylation cleanly to provide trans alkenes (3) whose isomeric purities equal or exceed those of 1.A mechanistic picture for this process which involves a carbenoid intermediate is presented.
Tellurium-zinc exchange reaction. A new preparative method of alkenylzinc reagents
Terao, Jun,Kambe, Nobuaki,Sonoda, Noboru
, p. 4741 - 4744 (2007/10/03)
Alkenyl tellurides were converted to the corresponding alkenylzinc compounds by the reaction with diethylzinc. The exchange reaction proceeds efficiently in THF at room temperature with retention of the stereochemistry of the starting tellurides. The successive reaction of the formed alkenylzinc with 4-iodotoluene in the presence of Pd(PPh3)4 afforded a cross-coupling product as a single stereoisomer.
Formation and Reactions of Olefins with Vicinal Silyl and Stannyl Substituents
Mitchell, T. N.,Wickenkamp, R.,Amamria, A.,Dicke, R.,Schneider, U.
, p. 4868 - 4874 (2007/10/02)
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
ORGANOCOPPER(I) MEDIATED SYNTHESIS OF 1-ALKENYLSILANES AND 1,3-ALKADIENYLSILANES FROM ETHYNYLSILANES
Westmijze, H.,Kleijn, H.,Vermeer, P.
, p. 317 - 324 (2007/10/02)
Ethynylsilanes (I) are converted into α-silyl substituted (Z)-alkenylcopper(I) compounds (II) by treatment with RCu reagents.The adducts II react with a variety of electrophiles to give the 1-alkenylsilanes RCH=C(E)SiR3' (III: E = H, Cl, Br, I, CN, SnMe3, SMe, Me, H2C=CHCH2).The conversion of I into III (E = H) can also be effected by using homocuprates, R2CuMgCl, and triorganodicuprates, R3Cu2MgCl.The latter reagent should be used when the group R is methyl.An interesting 1,3-diene formation is observed on treating excess of ethynyltrimethylsilane (Ib) with R3Cu2MgCl; this reaction involves addition of intermediary vinylcuprates to unreacted 1-alkynylsilane (Ib).The intermediary 1,3-dienyl adduct (VIIb) reacts with various electrophiles to give 1,3-dienes, RCH=C(SiMe3)CH=C(E)SiMe3 (VIIIb).
(E)- and (Z)-(1-Iodo-1-alkenyl)silanes. Their Preparation and Their Conversion ino (E)- and (Z)-(1-Lithio-1-alkenyl)silanes
Zweifel, George,Murray, Rex E.,On, Harry P.
, p. 1292 - 1295 (2007/10/02)
(Z)-(1-Iodo-1-alkenyl)trimethylsilanes can be conveniently obtained by isomerization of the readily available E isomers through the intermediacy of (1-lithioalkenyl)silanes formed by addition of catalytic amounts of tert-butyllithium.Reaction of (E)- and
