15336-98-8Relevant articles and documents
New simple route to allylstannanes by zinc-mediated coupling of allyl bromides with Bu3SnCl or Bu2SnCl2 in an H2O (NH4Cl)/THF medium
Carofiglio, Tommaso,Marton, Daniele,Tagliavini, Giuseppe
, p. 2961 - 2963 (1992)
A new zinc-mediated coupling reaction of allyl and allyl-like bromides with Bu3SnCl (1) or Bu2SnCl2 (2), performed in H2O (NH4Cl)/THF medium, represents an easy route to the following organostannanes: Bu3SnCH2CH=CH2 (3) and Bu2Sn(CH2CH=CH2)2 (4), Bu3Sn(C4H7) (5) and Bu2Sn(C4H7)2 (6) (where C4H7 stands for trans-crotyl, cis-crotyl, or α-methylallyl), and Bu3SnCH=C=CH2 (7). This striking one-pot procedure successfully improves the already general routes where Grignard or other conventional organometallic reagents are used.
A novel mode of access to polyfunctional organotin compounds and their reactivity in Stille cross-coupling reaction
Lamandé-Langle, Sandrine,Abarbri, Mohamed,Thibonnet, Jér?me,Duchêne, Alain
, p. 2368 - 2374 (2009/09/30)
Mono-, di-, tri- and tetra-functional organotin compounds were easily prepared in a sonicated Barbier reaction using ultrasound technology via coupling reaction of organo halides with tin halides (Bu3SnCl, Bu2SnCl2, BuSnCl
Wurtz-type reductive coupling reaction of allyl bromides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to allylstannanes and hexaaryldistannanes
Von Gyldenfeldt, Friederike,Marton, Daniele,Tagliavini, Giuseppe
, p. 906 - 913 (2008/10/08)
Twenty-one allylstannanes have been prepared via a simple Wurtz-type coupling reaction of allyl bromides and R3SnX compounds (R = Me, Et, Pr, Bu, Ph; X = Cl, I, OH), Bu2SnCl2, and (Bu2SnCl)2O in cosolvent/H2O (NH4Cl saturated) media under the mediation of zinc powder. Also R3SnSnR3 compounds (R = Ph, p- and m-Tol) have been prepared via coupling of triaryltin chlorides. The stereochemical course of the reaction between R3SnCl and (C4H7)Br (C4H7 = α-methylallyl, trans- and cis-crotyl) has been extensively studied. Two distinct reactions are involved in the overall process: (i) the coupling reaction, which gives rise stereoselectively to the sole R3SnCH(CH3)CH=CH2 (α-isomer), and (ii) the subsequent isomerization of the α-isomer furnishing mixtures of (α, trans, cis)-isomers. The occurrence of reaction ii depends upon the nature either of the R group or the employed cosolvent. In cyclohexane, the α-isomer is exclusively obtained with R = Bu, while with R = Me, Et, and Pr it is found as a major component in the ternary isomeric mixture. In tetrahydrofuran, 2-propanol, acetonitrile, and pyridine, the isomerization occurs to an extent which depends on the polarity and the coordinating ability of the cosolvent itself. The observed stereoselection has been hypothesized to occur through one-electron transfer from the zinc metal to the (C4H7)Br to form stereoselectively an adsorbed CH2=CHCH(CH3)Br?-Zn?+ radical ion which is trapped by the R3SnCl reactant to form the α-isomer. Similarly, ditin compounds are thought to be formed by interaction of R3SnCl?-Zn?+ radical ions with R3SnCl molecules.
