16630-96-9Relevant academic research and scientific papers
SELECTIVITY IN REACTIONS INVOLVING α-ALKOXYALLYLTRIBUTYLTINS
Quintard, Jean-Paul,Dumartin, Gilles,Elissondo, Bernard,Rahm, Alain,Pereyre, Michel
, p. 1017 - 1028 (2007/10/02)
The behaviour of α-alkoxyallyltributyltins has been studied in terms of chemo-, regio- and stereoselectivity.Chemoselectivity is readily controlled by the experimental conditions, as exemplified by the reaction of p-bromobenzaldehyde with α-ethoxycrotyltr
STEREOSELECTIVE FORMATION OF (E)-1-ALKENYL ETHERS. THE COUPLING REACTION OF 1,3- OR 3,3-DIETHOXY-1-PROPENE WITH GRIGNARD REAGENTS CATALYZED BY NICKEL-PHOSPHINE COMPLEX
Sugimura, Hideyuki,Takei, Hisashi
, p. 351 - 354 (2007/10/02)
1,3- or 3,3-Diethpxy-1-propene reacted with Grignard reagents in the presence of nickel-phosphine complex to give (E)-1-alkenyl ethers stereoselectively.
REACTIVITY OF α,β-UNSATURATED ACETALS AND KETALS TOWARD ORGANOLITHIUM REAGENTS IN PENTANE
Mioskowski, Charles,Manna, S.,Falck, J. R.
, p. 519 - 522 (2007/10/02)
Depending upon structure and reaction conditions, α,β-unsaturated acetals and ketals react with organolithium reagents in pentane by addition, substitution, or proton abstraction.
(α-Ethoxyalkenyl)tins: New Reagents for the Synthesis of Carbonyl Compounds
Quintard, Jean-Paul,Elissondo, Bernard,Pereyre, Michel
, p. 1559 - 1560 (2007/10/02)
(α-Ethoxybutenyl)tributyltin and (α-ethoxyallyl)tributyltins, obtained from the appropriate Grignard reagents and (chloroethoxymethyl)tributyltin, have been used for the synthesis of carbonyl compounds via enol ethers or monoprotected 1,2-diols.
Palladium-Catalyzed Cross-Coupling of (2-Ethoxyvinyl)boranes with Aryl and Benzyl Halides. A New Method for Conversion of Organic Halides into Aldehydes with Two More Carbon Atoms
Miyaura, Norio,Maeda, Koji,Suginome, Hiroshi,Suzuki, Akira
, p. 2117 - 2120 (2007/10/02)
Vinyl ethers 3 can be synthesized in high yields by the cross-coupling of an aryl or benzyl halide with tris(2-ethoxyvinyl)borane (1) or (2-ethoxyvinyl)-1,3,2-benzodioxaborole (2) in the presence of 1 mol percent of a palladium complex such as PdCl2(PPh3)2, Pd(OAc)2(PPh3)2, or Pd(PPh3)4 and a base while retaining the original configuration of the double bond in (2-ethoxyvinyl)boranes.No noticeable quantities of biaryls or conjugated dienes were found in this reaction.The reaction did not proceed in the absence of a base.This new vinyl ether synthesis was found to be applicable to aryl halides substituted with a variety of functional groups such as halogen, methoxy, carboethoxy, and acetyl groups.Electron-attracting substituents facilitate the coupling.Since vinyl ethers 3 thus obtained can readily be hydrolyzed to give aldehydes (eq 4), the sequence (eq 1-4) provides an efficient new method for converting an aryl halide into an aldehyde with two more carbon atoms.
