Triethyltins

Triethyltin hydroxide [994-32-1] M 222.9. Treated with HCl, followed by KOH, and filtered to remove diethyltin oxide [Prince J Chem Soc 1783 7959]. 

To obtain a product free from traces of triethyltin halide the dried ethereal solution is treated with dry ammonia, and the precipitate formed is removed by filtration. 

Buten-l -ynyidiethylaluminium Dimethyl-phenylethynylthallium 3-Buten-l -ynyltriethyllead 3-Methyl-3-buten-l -ynyltriethyllead 3-Buten-l -ynyidiisobutylaluminium Bis(Triethyltin) acetylene... 

Compared with the alkaline conditions used in the above methods, the removal of the triethylstannylic group (triethyltin) occurs for 3(5)-triethylstannylethynylpyra-zole at room temperature in CCI4 solution in the presence of acetic acid (71ZOB 2230) (Scheme 99). 

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). 

The earliest work in this field, by Cremer (466), showed that tetra-ethyltin is metabolized in vitro and in vivo (rats) to a triethyltin derivative and, later, it was further demonstrated that triethyltin compounds are converted in vitro into diethyltin derivatives (500). The latter are broken down in vivo to monoethyltins, which are eliminated from the body within a short time (501). Other trialkyltins appear to behave similarly (500). 

Helium MIP-MS is also a very sensitive detection system for organotin compounds, such as tetraethyltin (TET), tetrabutyltin (TBT), triethyltin bromide (TET-Br), tripropyltin chloride (TPT-C1), tributyltin chloride (TBT-C1), and others, separated by CGC [213]. Detection limits at sub-pg levels were achieved, and linear dynamic ranges of at least three orders of magnitude were obtained. 

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... 

The reaction of 95 with Me3SiC=CMe shows clearly that the B-CHEt bond is more reactive than the BCH2 bond, and the products (E)-96 and (E)-97 are formed in a 1 1 ratio (note that there are 2BCH2 bonds in 95). In the case of the tert-butyl derivative, steric factors control the process. Moreover, repulsion between the Et and SnMe3 substituents results in the preferential formation of (Z)-99 <2001JOM(620)51>. On the other hand, reaction with bis(triethyltin)ethyne gives only product (Z)-100 (Scheme 38) <2003JOM(687)108>. 

Disproportionation to form tetraethyltin was observed when triethyltin cyanoacetate was heated (50). The fate of the cyanoacetate group was not established. 

In 1954, a proprietary formulation, Stalinon , was marketed in France for oral administration of boils. The formulation was primarily linoleic acid but was contaminated with triethyltin (TET)iodide (LD50 in rats, ca 0.7 mg/kg1) and may have contained the mono-, di- and tetraethyltin compounds. The formulation led to the death of 102 people and the intoxication of more than 200 others. The TET caused altopic cerebral edema of the white matter of the brain. Since the Stalinon Affair , a great deal of control has been exerted in the manufacture and marketing of organotins and few deaths have occurred11. The accidental exposure of six industrial workers to TMT led to one death and to two seriously... 

Tin is comparable in its toxicological behavior to lead and mercury. Bivalent tin compounds generally are more toxic than the tetravalent compounds. Furthermore, organic tin compounds are more toxic than inorganic ones and the trialkyl analogs (triethyltin, trimethyltin, tributyltin) are the most toxic. As the number of carbon atoms attached to tin increases, the toxicity of the organic tin compounds rapidly declines9,77. 

Effects of triethyltin on brain octamines and their metabolism in the rat has been investigated104. 

As mentioned before, the diethyl-, triethyl- and tetraethyltin compounds were dealky-lated to give rise to ethylene as a major product and ethane as a minor product with liver microsomal fractions, NADH and oxygen27. Tetraethyltin was found to be converted into triethyltin salts in significant concentrations. 

Triethyltin injections (4 intramuscular injections, 2 weeks apart) at 1.75 mg/kg BW resulted in total suppression of pecking behavior for 3 h recovery under way by 27 h postinjection (Idemudia and McMillan 1986a)... 

Single oral dose of 3 mg triethyltin sulfate/kg BW resulted in immediate collapse, salivation, convulsions, and death in a few min at 2 mg/kg, bird was unconscious for 1-1.5 h postadministration, with recovery beginning in 1 day (Stoner et al. 1955)... 

Feeding of 160 mg triethyltin hydroxide/kg diet for 15 weeks was not fatal, but caused muscular weakness and some diet avoidance (Stoner etal. 1955) Acute oral LD50 of tricyclohexyltin hydroxide varies between 255 and 390 mg/kg BW dietary levels of 20 mg/kg had no measurable effect on growth, survival, or reproduction (Zuckerman etal. 1978)... 

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