18752-22-2Relevant academic research and scientific papers
Convenient synthesis of isoxazolines via tandem isomerization of allyl compounds to vinylic derivatives and 1,3-dipolar cycloaddition of nitrile oxides to the vinylic compounds
Krompiec, Stanis?aw,Bujak, Piotr,Szczepankiewicz, Wojciech
supporting information; experimental part, p. 6071 - 6074 (2009/04/11)
A novel effective method for the synthesis of new isoxazolines via tandem isomerization of QCH(X)CH{double bond, long}CH(Y) to QC(X){double bond, long}CHCH2(Y) (Q = RO, RS, R2N, R3Si, etc.; X = H, R, OR; Y = H, R; R = alkyl, aryl) catalyzed by ruthenium complexes and 1,3-dipolar cycloaddition of the latter compounds to arenenitrile oxides is presented. The cycloaddition of QCH(X)CH{double bond, long}CH(Y) to 2,6-dichlorobenzonitrile oxide is also described. The regio- and stereoselectivity of the cycloaddition of nitrile oxide to allyl and 1-propenyl (vinylic in general) compounds is discussed.
Regioselective Protonation of Allylithium Compounds
Luening, Ulrich,Wangnick, Carsten,Kuemmerlin, Martin
, p. 2431 - 2434 (2007/10/02)
By varying the general acid, the regioselectivity of the protonation of (triphenylsilyl)allyllithium (1) in diethyl ether in the presence of HMPT can be changed from 9:1 to 1:9 at room temperature.When other aprotic solvents are used, the nature of the lithium salt changes, and the selectivity decreases.The regioselectivity of the protonation of the dithio-stabilized allyllithium 4 by water is highly dependent on the age of the allyllithium solution with α/γ ratios varying from 2.7:1 to 1:3.5. - Key Words: Protonation, regioselective / Allyllithium compound / Allyl anion / General acid / Regioselectivity / Aging
Preparation of (Triphenylsilyl)allyl Anion and (Triphenylgermyl)allyl Anion from 1-Propenyltriphenylsilane and 1-Propenyltriphenylgermane and Their Reactions with Electrophiles
Wakamatsu, Kuni,Oshima, Koichiro,Utimoto, Kiitiro
, p. 2029 - 2032 (2007/10/02)
Treatment of 1-propenyltriphenylsilane with n-BuLi in THF-HMPA provides (triphenylsilyl)allyl anion which is identical with an anion derived from 2-propenyltriphenylsilane and base.Generation of (triphenylgermyl)allyl anion is also described.Addition of alkyl halides or carbonyl compounds to these anions gives the corresponding adducts regioselectively.
