92544-41-7Relevant academic research and scientific papers
Lewis acid-catalyzed three-component condensation reactions of aldehydes, alkoxysilanes, and propargylsilane: Synthesis of α-allenyl ethers
Niimi, Lui,Shiino, Keitaro,Hiraoka, Shuichi,Yokozawa, Tsutomu
, p. 1721 - 1724 (2001)
For simultaneous construction of a polyether backbone and the allenyl side chains, Lewis acid-catalyzed three-component condensation reactions of aldehydes, alkoxytrimethylsilanes, and 1-trimethylsilyl-2-butyne were studied. The reaction of these three compounds took place in the presence of a catalytic amount of TrClO4 at -78°C to yield the corresponding α-allenyl ethers in good yields. This reaction was also applied to the synthesis of a polyether having allenyl side chains.
Subtle electronic effects in metal-free rearrangement of allenic alcohols
Sabbasani, Venkata R.,Mamidipalli, Phani,Lu, Huijie,Xia, Yuanzhi,Lee, Daesung
supporting information, p. 1552 - 1555 (2013/06/26)
A general and stereoselective rearrangement of allenic alcohols to (E,E)-1,3-dien-2-yl triflates and chlorides was developed under metal-free conditions. Subtle electronic effects of the alkyl and aryl substituents on the carbon bearing the hydroxyl group has a profound impact on the reaction rate and efficiency such that vinyl triflates were obtained from electron-deficient substrates and trimethylsilyl triflate whereas vinyl chlorides were generated with an electron-rich substrate and trimethylsilyl chloride.
Synthesis of 4-aryl- and 4-alkyl-2-silyl-1,3-butadienes and their Diels-Alder/cross-coupling reactions
Junker, Christopher S.,Welker, Mark E.,Day, Cynthia S.
scheme or table, p. 8155 - 8165 (2011/03/18)
An ene-yne cross methasis of silyl-substituted alkynes and alkenes has been developed as a route to 4-aryl- and 4-alkyl-2-silyl-substituted 1,3-dienes. The dienes prepared were used to affect highly diastereoselective Diels-Alder reactions and then the silicon-substituted Diels-Alder cycloadducts were used in Hiyama cross-coupling reactions. The cross-coupling reactions enable these silicon dienes to be used as synthons for a variety of other dienes one might prepare and need access to. Two of the silicon-substituted Diels-Alder cycloadducts and one of the Hiyama cross-coupling products were also characterized by X-ray crystallography.
Preparation of 1,3-dienyl organotrifluoroborates and their Diels-Alder/cross-coupling reactions
De, Subhasis,Day, Cynthia,Welker, Mark E.
, p. 10939 - 10948 (2008/02/12)
2-BF3-substituted 1,3-butadienes with potassium and tetrabutyl ammonium counterions have been prepared in gram quantities from chloroprene via a simple synthetic procedure. The potassium salt of this new main group element substituted diene has
A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents
Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Torre, Giovanni,Prati, Fabio
, p. 2216 - 2219 (2007/10/03)
A new application of (PhO)3P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.
A very simple synthesis of chloroalkenes and chlorodienes by selective Suzuki couplings of 1,1- and 1,2-dichloroethylene
Barluenga, Jose,Moriel, Patricia,Aznar, Fernando,Valdes, Carlos
, p. 347 - 353 (2007/10/03)
Chloroalkenes, important building blocks for cross-coupling reactions, are prepared in one step by the Suzuki reaction of 1,1-dichloroethylene and 1,2-dichloroethylene with alkenyl- and arylboronic acids. Under the proper reaction conditions, it is possible to obtain the monocoupling reaction to provide the corresponding chloroalkenes with good yields. This method represents an excellent route for the preparation of chloroalkenes and chlorodienes from commercially available starting materials.
Unexpected SN2'-type addition-elimination reactions of 1-aryl-2,3-allenols with LiX. Synthesis and synthetic application of 1-aryl-3-halo-1,3-dienes
Ma, Shengming,Wang, Guangwei
, p. 5723 - 5726 (2007/10/03)
1-Aryl-3-halo-1,3-dienes were prepared from the sequential addition-elimination reaction of 1-aryl-2,3-allenols with LiX (X=Br, Cl) in HOAc in moderate to good yields. Here the aromatic substituent is crucial to this interesting transformation since no re
