Diphenyltin oxide

The triprotic corroles 64 form monoorganotin complexes of the type RSnlv(Cor). PhSn(Cor) is formed when octaethylcorrole reacts with diphenyltin oxide, or phenylmagnesium bromide reacts with ClSn(Cor). The tin is five-coordinate, and is placed 72.2(3) pm above the plane of the four nitrogen atoms, with the corrole assuming a domed structure. The compound is reversibly reduced by transfer of one electron into the 7r-system.511... 

Octaethylcorrole, H3(Oec) reacts with diphenyltin oxide to give PhSn(Oec), and the same product is formed from the phenylation of ClSn(Oec) with phenylmagnesium bromide (equation 16.55).51 The corrole adopts a domed conformation (16-16), and the 5-coordinate tin atom is 72.2(3)pm above the average plane of the four nitrogen atoms, with rSnC 210.5 pm. 

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). ... 

Triphenyltin nitrate has poor stability, and decomposes at quite low temperatures to nitrobenzene and diphenyltin oxide"". ... 

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 ... 

Bis(tributyltin)oxide in antifouling paint was found to change to tributyltin chloride and an unknown organotin species by Allen and coworkers106. The organotin species appear to be held strongly within the paint film. In the case of triphenyltin chloride and triphenyltin acetate, evidence of dephenylation to form diphenyltin and monophenyltin compounds has been obtained. 

Diphenyltin dihydride, 224 Diphosphorus tetraiodide, 224-225 (+ )-Di-3-pinany Iborane, 225-226 Diprenyl ether, 160 Dipyridinc chromium(VI) oxide, 139 DisiamyIborane, 226 N,N -Disuccinimjdyl carbonate, 226-227... 

Compounds according to entries 1, nitrato-triphenyl-(pyridine-N-oxide)tin 2, (l,2-benzisothiazol-3(2//)-one-l,l-dioxide)-(quinoline-N-oxide)triphenyltin 3, chloro-(2,6-dimethylpyridine-N-oxide)trimethyltin 4, dichloro-(2,6-dimethylpyridine-N-oxide)diphenyltin 5, (coumarin-3-carboxylato)(quinoline-N-oxide)triphenyltin 6, isocyanato-(pyridine-N-oxide-O)-triphenyltin 7, bis(A,A)-dimethyldithiocarbamoylKacetato-0)(quinoline-N-oxide)tnphenyl-tin 8, (isopropylxanthato)(quinoline-N-oxide)triphenyltin. 

Very recently a family of diphenyltin(IV) compounds was tested in vitro against human tumor cell lines to assess their cytotoxic activity, and the same family of compounds was also tested for antioxidant efficiency in rat brain homogenate, showing that there is a structure-activity relationship in the latter case. The correlation suggests that selected molecular variables are prototype tracers for the calculation of inhibitory concentrations. Moreover there seems to be an inverse structure-response behavior among activities, since the most hydrophobic organotin molecule is the least active compound for cytotoxic assays, while it is the best in anti-oxidant tests. 

Figure 7.3. Separation of organotin compounds on a 10 cm x 1 mm I.D. column packed with Deltabond Methyl with supercritical fluid carbon dioxide saturated with formic acid as mobile phase. The separation was obtained at 60°C using pressure programming 0.5 min hold at 90 atm. Then programmed at 4 atm / min to 150 atm where the program rate was increased to 10 atm / min to 300 atm. Peak identification 1 = dibutyltin dichloride 2 = tributyltin chloride 3 = tetrabutyltin 4 = diphenyltin dichloride 5 = dicyclohexyltin dichloride 6 = bis(tributyltin) oxide 7 = triphenyltin chloride 8 = tricyclohexyltin chloride 9 = tetraphenyltin 10 = tetracyclohexyltin 11 = bis(triphenyltin) oxide and 12 = hexakis(2-methyl-2-phenylpropyl) distannoxane. (From ref. [42] Springer-Verlag)...

Five oiganotin compounds used as pesticides or PVC stabilizers (fenbutatin oxide, triphenyltin chloride, tricyclohexyltin hydroxide, di-n-butyltin dichloride and diphenyltin dichloride) were baseline resolved on a cyanopropyl column (A = 430nm, ex 495nm, em) using a 96/2/2 hexane/THF/acetic acid mobile phase [809]. Detection limits of 1-2 ng injected for standards, 20-30 ng/L for surface water, and 200-300 ng/g for soils were obtained when a postcolumn irradiation/morin (3,5,7,2, 4 -pentahydroxyflavone) reaction was used. 

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