66270-74-4Relevant academic research and scientific papers
Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt
Takai, Kazuhiko,Kunisada, Yuji,Tachibana, Yukiko,Yamaji, Nana,Nakatani, Emi
, p. 1581 - 1586 (2007/10/03)
(Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl 3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR) 2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.
Synthesis of (Z)-vinylsilanes with high diastereoselectivity by using samarium diiodide
Concelloen, Jose M.,Bernad, Pablo L.,Bardales, Eva
, p. 937 - 939 (2007/10/03)
matrix presented β-Elimination of O-acetyl 1-chloro-1-trimethylsilylalkan-2-ols 1 was achieved by using samarium diiodide as a metaling reagent and afforded the corresponding (Z)-vinylsilanes with high stereoselectivity. The starting compounds 1 were easi
One-pot transformation of RCHO to (E)-RCH=CHSiMe3 using CHI3, Mn, Me3SiCl, and a catalytic amount of CrCl2
Takai, Kazuhiko,Hikasa, Shintaro,Ichiguchi, Tetsuya,Sumino, Naoki
, p. 1769 - 1771 (2007/10/03)
Iodoform is reduced with manganese in the presence of Me3SiCl to give Me3SiCHI2 (1). A one-pot transformation of aldehydes to (E)-1- alkenyltrimethylsilanes is then performed with iodoform, manganese, Me2SiCl, and a catalytic amount of chromium(II) chloride in THF via in situ formation of 1.
Stereoselectivity of the Thermally Initiated Free-Radical Chain Addition of Cyclohexane to 1-Alkynes
Metzger, Juergen O.,Blumenstein, Michael
, p. 2493 - 2500 (2007/10/02)
Alkanes can be added to alkynes in a thermally initiated free-radical chain reaction ("ane reaction").The addition of cyclohexane to 1-alkynes 1a-l yields a mixture of (Z)- and (E)-2-cyclohexyl-1-alkenes 3a-l.An essential step in this reaction is the addi
The Hydroboration of (Trimethylsilyl)ethyne with Dialkylboranes and its Application to the Synthesis of (E)-1-(Trimethylsilyl)alk-1-enes and 2-(Trimethylsilyl)alk-1-enes
Hoshi, Masayuki,Masuda, Yuzuru,Arase, Akira
, p. 3237 - 3241 (2007/10/02)
The reaction of (trimethylsilyl)ethyne 1 with a stoicheiometric amount of dialkylborane 2 proceeds to the monohydroboration stage, giving a mixture of regioisomers, (E)-dialkylborane 3 and dialkylborane 4.In the hydroboration with bulky dialkylboranes, derived from internal alkenes, the former predominates.Successive treatment of the mixture with methyllithium and benzenesulphenyl chloride exclusively affords highly pure (E)-2-alkyl-1-(trimethylsily)ethene 6 whose alkyl group migrates from the boron atom, while in the hydroboration with less bulky dialkylboranes, derived from terminal alkenes, the latter predominates.Successive treatment of the mixture with aq.NaOH and iodine exclusively affords highly pure 2-(trimethylsilyl)alk-1-ene 7 whose alkyl group migrates from the boron atom.
STEREOSELECTIVE SYNTHESIS OF (E)-ALKENYLSILANES FROM ALDEHYDES WITH A REAGENT PREPARED BY CHROMIUM(II) REDUCTION OF Me3SiCHBr2
Takai, Kazuhiko,Kataoka, Yasutaka,Okazoe, Takashi,Utimoto, Kiitiro
, p. 1443 - 1446 (2007/10/02)
Aldehydes are converted to the corresponding (E)-alkenylsilanes with one carbon homologation by means of a gemdichromium reagent prepared by CrCl2 reduction of Me3SiCHBr2 in THF.Transformation of aldehydes into alkenyl sulfides is also achieved with a com
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
