Triethyltin hydride

Trimethyltin hydride has been shown to add to trimethylvinyltin, and triethyltin hydride to triethylvinyltin, to give both the 1,1- and the 1,2-distannylethanes, whereas triphenyltin hydride reacts with triphenyl vinyltin to give only the 1,2-adduct (180). 

Trimethyltin chloride reacts with carboxylic acids at 100° to give the corresponding chloride carboxylates Me2Sn(Cl)OCOR (187, 188), and diethyltin dihydride, triethyltin hydride, hexaethylditin, and bis(triethyltin) oxide have been shown to react with lead tetraacetate to give diethyltin diacetate or triethyltin acetate, as appropriate (189). 

Triethyltin hydride promotes the radical decomposition of 128 giving carbazole. The dimer 129 (R = H) decomposed in dry benzene at room temperature giving carbazole (10%) and 9-anilinocarbazole (20%) and other unidentified products. However 129 (R = Me) gave 130, which on warm-... 

A variety of synthetic methods employs tin hydrides as the starting materials. The interaction of triethyltin hydride with diethylmercury leads to hexaethylditin, mercury, and ethane 228). Hexamethylditin has been obtained by treatment of dimethyltin dihydride with sodium in liquid ammonia, followed by addition of methyl iodide. 

Triethyltin hydride reduces chlorodimethylarsine quantitatively to dimethylarsine 283a). Substituted arsenic hydrides are also produced by coupling and by hydrolysis reactions involving metal derivatives of arsenic hydrides 163, 284). 

The results of the last two experiments are of great importance. They show clearly that the lead hydrides have a higher reduction potential than the tin hydrides galvinoxyl (21) is not reduced by triethyltin hydride even at 70°-80° C (255), but is reduced by tributyl/ead hydride spontaneously at 0° C. Finally, triethyltzn chloride (22) can be reduced by tributyl/eaJhydride. (Under the same conditions reduction of X.nct y germanium chloride with tributylt/n hydride also takes place spontaneously.)... 

Powdered triethyltin fluoride added gradually with stirring at —30° to diethylaluminum hydride, and kept 2hrs. at 20° triethyltin hydride. Y <... 

In the addition reaction between triethyltin hydride and AT-benzyliden-p-toluidine, benzyl-p-tolylaminotriethyltin is formed 82, 83). 

The corresponding addition product of triethyltin hydride could not be isolated, although its formation was demonstrated by infrared studies and hydrolysis experiments. 

The reaction of tributyltin methoxide with isothiocyanate was reported to lead to the corresponding thiocarbamate. It is worthy of note that the adduct of triethyltin hydride and phenyl isothiocyanate contains a tin-sulfur rather than a tin-nitrogen bond (93, 94). 

Noltes and Janssen (93, 94) have prepared a number of formamide derivatives by the addition of organotin hydrides to organic isocyanates. Triethyltin hydride, for example, reacts at room temperature with an equimolecular amount of phenyl isocyanate to give triethyl(fV-phenyl-formamido)tin. 

The products obtained from the reaction between triethyltin methoxide and A -hexyl- or N-phenylformamide were found to be identical with those obtained previously by addition of triethyltin hydride to the corresponding isocyanates (93, 94). The organotin-substituted carbamates obtained by the amidolysis reaction and those obtained by the addition of triethyltin methoxide to the corresponding isocyanate are, likewise, identical. 

Another addition reaction important in this connection h that between triethyltin hydride and diethyl azodicarboxylate (84). Equimolecular amounts of these reactants in hexane solution spontaneously give on the one hand the reduction product diethyl hydrazinedicarboxylate and on the other hand a compound containing two triethyltin groups. It is assumed that the primary addition product very readily disproportionates. 

The H—D exchange between triethyltin deuteride and di-isobutylaluminum hydride has been studied by Neumann 84). A four-center transition state has been proposed for this reaction... 

For the determination of organotin compounds (tributyltin, triphenyltin, triethyltin, and tetra-ethyltin) a MAE is proposed before the normal phase (NP) HPLC/UV analysis [35], In organotin and arsenic speciation studies, hydride generation is the most popular derivatization method, combined with atomic absorption and fluorescence spectroscopy or ICP techniques [25,36], Both atmospheric pressure chemical ionization (APCI)-MS and electrospray ionization ESI-MS are employed in the determination of butyltin, phenyltin, triphenyltin, and tributyltin in waters and sediments [37], A micro LC/ESI-ion trap MS method has been recently chosen as the official EPA (Environmental Protection Agency) method (8323) [38] it permits the determination of mono-, di-, and tri- butyltin, and mono-, di-, and tri-phenyltin at concentration levels of a subnanogram per liter and has been successfully applied in the analysis of freshwaters and fish [39], Tributyltin in waters has been also quantified through an automated sensitive SPME LC/ESI-MS method [40],... 

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