- Diorganostannide dianions (R2Sn2-) as reaction intermediates revisited: In situ 119Sn NMR studies in liquid ammonia
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It has frequently been proposed that diorganostannide dianions, SnR 22-, form during reactions of dihalodiorganostannanes or dihydrodiorganostannanes with sodium in liquid ammonia. The formation of this intermediate has been advanced to be an important step in the synthesis of a wide range of organostannanes. Here we report 119Sn NMR investigations in liquid NH3 of reaction intermediates that formed in situ during the conversions of dichlorodiphenylstannane, dihydrodiphenylstannane (diphenylstannane), dideuterodiphenylstannane, and dichlorodibutylstannane, respectively. This study revealed that the proposed SnR22- dianion was not present, but tetraorganodistannides, (R2Sn-SnR2)2-, and hydrodiorganostannides (tin hydrides), R2SnH- (or R 2SnD-, respectively), were detected instead.
- Trummer, Markus,Caseri, Walter
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p. 3862 - 3867
(2010/12/24)
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- A novel mode of access to polyfunctional organotin compounds and their reactivity in Stille cross-coupling reaction
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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
- Lamandé-Langle, Sandrine,Abarbri, Mohamed,Thibonnet, Jér?me,Duchêne, Alain
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p. 2368 - 2374
(2009/09/30)
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- Wurtz-type reductive coupling reaction of primary alkyl iodides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to mixed alkylstannanes and hexaalkyldistannanes
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Mixed tetra-alkylstannanes R3SnR′ (R = Et, n-Pr, n-Bu and R′= Me, Et, n-Pr, n-Bu, n-Pent) and R2SnR′2 (R = n-Bu and R′ = Me, Et, n-Pr, n-Bu) can be easily prepared in a one-pot synthesis via coupling reaction of alkyl iodides R′I with R3SnX (X = Cl, I) and R2SnCl2 compounds in cosolvent-H2O(NH4Cl) medium mediated by zinc dust. Coupling also occurs with (Bu3Sn)2O. It has been verified that reactions are possible only with primary alkyl iodides; with secondary alkyl iodides the coupling reaction fails. When alkyl chlorides and bromides are used ditin compounds are obtained instead of the unsymmetrical tetra-alkylstannanes. This represents a route to hexaalkyldistannanes.
- Marton, Daniele,Tari, Massimo
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- SYNTHESE UND UMLAGERUNGSREAKTIONEN VON o-FUNKTIONELLEN PHENYLLITHIUM- UND PHENYLNATRIUM DERIVATEN DER IVB UND VB-ELEMENTE
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While o-substituted bromobenzene derivatives of the type o-BrC6H4XERn (X = O, S; ERn = SiMe3) and n-BuLi undergo metal halogen exchange followed by silyl-X -> C rearrangement, the corresponding compounds of phosphorus, arsenic or tin are split at the E-X bond. o-Metal derivatives o-MI-C6H4XERn (X = O, NMe; E = P, As, Sn) of these elements may be generated, however, by direct reaction with sodium or lithium.They are unstable and furnish o-hydroxy- and o-aminophenyl element(IV, V) derivatives via an intramolecular anionic rearrangement.
- Heinicke, J.,Nietzschmann, E.,Tzschach, A.
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