Diphenyltin hydride

The oxidation in the last two reactions explains the anodic peak. Under the second cathodic wave an overall four-electron reduction yields a diphenyltin polymer and diphenyltin hydride ... 

Diphenyltin hydride Ph2SnH2 is stable in methanol. Polarography in MeOH/O.l M LiCl shows two oxidation waves which are to some extent dependent on the electrolyte. E /2 values are —0.27 and —0.12 (V vs SCE). The oxidation is shown by LSV to follow the reaction96 ... 

The diphenyltin hydride derived from 4-vinylpyridine has the advantage that the resulting tin halide sticks to the baseline during column chromatography on silica Rf of ca. 0) eluted with 1 3 ethyl acetate hexane, allowing easy separation from non-polar products. " Residual reagent has an R/ of ca. 0.2 compared to an of ca. 0.9 for Iriphenyltin hydride. 

The mixed halide-hydrides PhjSnHCl and PhjSnHBr have been prepared from the reaction of diphenyltin dihydride with the appropriate diphenyltin dihalides (274). 

In a modification of this method, the Sn-0 bonded compound can be generated in situ by partial acidolysis of a tin hydride, and, from the reaction between diphenyltin dihydride and carboxylic acids, a number of l,2-bis(acyloxy)-l,l,2,2-tetraphenylditins, (RC02)Ph2SnSnPh2(02CR) (e.g., R = CHj, CF3, PhaSi, or PhjGe), have been prepared (257, 258). 

Monohalomonohydrotin compounds can be prepared in excellent yields by reactions of triphenyltin hydrides with dialkyl- or diphenyltin dihalides345 ... 

The mixed hydride chlorodiphenylstannane also forms by an exchange reaction with diphenyltin chloride and, in turn, converts rapidly to the dimer ... 

REDUCTION, REAGENTS Aluminum amalgam. Borane-Dimethyl sulfide. Borane-Tetrahydrofurane. t-Butylaminoborane. /-Butyl-9-borabicyclo[3.3.1]nonane. Cobalt boride— f-Butylamineborane. Diisobutylaluminum hydride. Diisopropylamine-Borane. Diphenylamine-Borane. Diphenyltin dihydride. NB-Enantrane. NB-Enantride. Erbium chloride. Hydrazine, lodotrimethylsilane. Lithium-Ammonia. Lithium aluminum hydride. Lithium borohydride. Lithium bronze. Lithium n-butylborohydride. Lithium 9,9-di-n-butyl-9-borabicyclo[3.3.11nonate. Lithium diisobutyl-f-butylaluminum hydride. Lithium tris[(3-ethyl-3pentylK>xy)aluminum hydride. Nickel-Graphite. Potassium tri-sec-butylborohydride. Samarium(II) iodide. Sodium-Ammonia. Sodium bis(2-mcthoxyethoxy)aluminum hydride. 

The reagent is prepared in ether solution by reduction of diphenyltin dichloride (Metal and Thermit Corp.) with lithium aluminum hydride. It can be isolated by crystallization from petroleum ether-methylene chloride, but solutions in benzene are only moderately stable at room temperature. 

Diphenyltin dihydride reduces aldehydes and simple ketones to alcohols in yields of about 80%, and the reaction differs from reduction with a metal hydride in that a >C=0 + (CsHjljSnHj ------------------------- CHOH + CsHsljSn... 

Diphenyltin dihydride was found to be effective for reduction of 1,4,7,7-tetrachloronorbomane (1) to 1,4-dichloronorbomane (2). Use of tri-n-butyltin hydride led only to reduction to 1,4,7-trichloronorbomane.2... 

An ethereal soln. of diphenyltin dichloride added at —5° to an ethereal soln. of diethylaluminum hydride, and stirred 2 hrs. at —20° -> diphenyltin dihydride. Y 81%. Neumann and H. Niermann, A. 653,... 

Bromodiphenylstannane, loci Diphenylbromostannane. Diphenyltin bromide hydride [3300-53-6]... 

Soderguist and Crosby have developed a method for the simultaneous determination of triphenyltin hydroxide and its possible degradation products tetraphenyltin, diphenyltin oxide, benzenestan-noic acid, (and inorganic tin) in water. The method is rapid (one sample set per hour), sensitive to less than 0.01 g/ml for most of the tin species and exhibits no cross-interferences between the phenyltins. The phenyltins are detected by electron capture gas-liquid chromatography after conversion to their hydride derivatives, while inorganic tin is determined by a procedure which responds to tin (IV) oxide as well as aqueous tin (IV). ... 

Diphenyltin dihydride (Ph2SnH ). Using the procedure described above, reaction of 3.4g of diphenyltin dichloride (Research Chem.) and l.lg of lithium aluminium hydride gave 2.1g (75% yield) of a clear liquid (lit. bp 89-93°C/0.3 Torr) with the following characteristics 1.6127 (lit. 1.595 IR 1865 cm (Sn-H)(lit. 

The first of these methods with di- -butyltin or di- -propyltin hydride and phenylacetylene gives a viscous oil in the latter case the average value of is 11 37,59). The polymeric adduct which is formed in the corresponding reaction involving diphenyltin dihydride is a hard, brittle solid (59). 

The first observation, of the reduction of a ketone by an organotin hydride appears to have been the result of an attempt to carry out the hydrostarma-tion of 2 moles of methyl vinyl ketone by 1 mole of diphenyltin dihydride (63, 64). Instead of the expected adduct the products were pol5rmeric diphenyltin, which precipitated during the reaction, and methyl vinyl carbinol, Eq. (32). This reaction is surprising because the alcohol is isolated... 

Among the other simple compounds reduced by diphenyltin dihydride are cyclohexanone (82%), benzaldehyde (62%), mesityl oxide (60%), and chalcone (75%). It can be seen that the yields are high with the simple ketones and aldehydes, and moderate in the case of the a,]8-unsaturated analogs. The cause of the lower yields has not been examined, but may be due to the occurrence of hydrostannation, particularly of the product alcohol, as a side reaction. In all of these cases the unsaturated alcohol was the reduction product the double bond was not reduced. The same is true when triphenyltin hydride is used in the reduction of methyl vinyl ketone and phenyl vinyl ketone 66). 

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