Tin, tributyl

In a similar way HjC=C=C(0CH3)(SnBuj), n 1.4955 (undistilled) was prepared in almost quantitative yield from 0.12 mol of butyllithium in 75 ml of hexane and 75 ml of diethyl ether, 0.14 mol of methoxyallene and 0.10 mol of tributyl-tin chloride. The product contained 8-10% of an impurity, possibly Bu3Sn-CH2CEC-0CH3. 

Boron, as barium metaborate, is marketed as a mildew preventative for paints (273). Borax is used as a wood preservative, and an organic boron, 2,2 -(l-methyltrimethylenedioxy)-bis(4,4,6-trimethyl)-l,3,2-dioxaborinane (Biobor JF) [14697-50-80] is a biocide for jet fuel (274). Whereas tin metal is used to coat steel cans used as food containers, organic tin in the form of tributyl tin compounds have proven to be powerfiil antimicrobials, and have found use in antifouHng coatings for ship bottoms, paints, and wood preservatives (275). 

Dissolve in Et20, add quinol (500mg for 300mL), dry over Na2S04, filter, evaporate and distil under dry N2. It is a clear liquid if dry and decompose very slowly. In the presence of H2O traces of tributyl tin hydroxide are formed in a few days. Store in sealed glass ampoules in small aliquots. It is estimated by reaction with aq NaOH when H2 is liberated. CARE stored samples may be under pressure due to liberated H2. [J Appl Chem 7 366 1957.]... 

A mixture of 23.4 g (39.3 mmol) of bis[(tributyl)tin] oxide and 11.6 g (81.7 mmol) of 4,6-dimethyl-l-hepten-4-ol is heated at 220 CC for 10 h in a three-necked flask equipped with a 12-cm Vigreux column, a condenser, a thermostat, and separating funnel. During this time a further 11.6 g (81.7 mmol) of 4,6-dimethyl-1-hcp-ten-4-ol are added dropwisc, and 4-methyl-2-pentanone (approx. 16 g) distilled out. The residue is distilled yield 11.5 g (88%) bp 92-93 °C/0.3 Torr. 

These results are in accordance with the findings of Boothe and coworkers26, who found that the reactions of four diastereomeric 2-bromo-3-phenylsulfinylbutanes with tributyl-tin radicals generate /3-phenylsulfinyl sec-butyl radicals (8) which eliminate PhSO radicals to form the 2-butenes in a stereoselective manner. The stereoselectivities observed in this free radical elimination must result from the fact that the rate constant for elimination is greater than that for rotation about the C—C bond. Furthermore, a neighboring phenyl group on the radical center seems to stabilize the radical enough so that the internal rotation can compete with the -elimination reaction. It is also noteworthy that the small... 

Unfortunately, processes are not always so simple. The members of groups such as polychlorinated biphenyls (PCBs) and PAHs, for example, do not all operate through the same principal mechanism of action. Also, some individual pollutants such as p,p -DDT or tributyl tin work through more than one mode of action. 

Bryan, G.W., Gibbs, P.E., Hummerstone, L.G., and Burt, G.R. (1986). The decline of the gastropod Nucella lapillus around Southwest England—Evidence for the effect of tributyl-tin from antifouling paints. Journal of the Marine Biological Association of the United Kingdom 66, 611-640. 

Marcillo, Y., Ronis, M.J.J., and Porte, C. (1998). Effects of tributyl tin on the phase 1 testosterone metabolism and steroid titres of the clam. Aquatic Toxicology 42, 1-13. 

Mensink, B.P. (1997). Tributyl Tin causes Imposex in the Common Whelk Mechanism and Occurrence NIOZ RAPPORT 1997-6 Nederlands Institut voor Onderzoek der Zee. 

Morcillo, Y., Janer, G., and O Hara, S.C.M. et al. (2004). Interaction of tributyl tin with cytochrome P450 and UDP glucuronyl transferase systems of fish in vitro smdies. Environmental Toxicology and Chemistry 23, 990-996. 

Shimasaki, Y., Kitano, T., and Oshima, Y. (2003). Tributyl tin causes masculinisation of fish. Environmental Toxicology and Chemistry 22, 141-144. 

Fractional separation of tin compounds used as stabilisers in PVC was based on substoichiometric isotope dilution analysis [446]. The tin compounds were isolated by extraction and complexed with salicylideneamino-2-thiophenol, followed by controlled addition of y-irradiated tributyl tin oxide and measurement of the y-activity. PVC containing a nominal 0.63% (Bu Sn analysed 0.614 0.016% in nine determinations. 

An early - but mechanistically interesting - construction of a bicyclo[3.1.0]oxa-hexane by a domino radical cyclization was presented by Luh s group [50]. The addition of tributyl tin and AIBN to a solution of bromides 3-111 in refluxing benzene gave 3-114 as single diastereoisomers in acceptable yields via the intermediates 3-112 and 3-113 (Scheme 3.29). It is important that the cyclopropyl carbinyl radical intermediate has the correct stability and reactivity, which is achieved by the a-silyl substituent. 

Laughlin et al. [122] analysed chloroform extracts of tributyltin dissolved in seawater using nuclear magnetic resonance spectroscopy. It was shown that an equilibrium mixture occurs which contains tributyltin chloride, tributyl tin hydroxide, the aquo complex, and a tributyltin carbonate species. Fluorometry has been used to determine triphenyltin compounds in seawater [123]. Triph-enyltin compounds in water at concentrations of 0.004-2 pmg/1 are readily extracted into toluene and can be determined by spectrofluorometric measurements of the triphenyltin-3-hydroxyflavone complex. 

Hamasaki and coworkers87 investigated the genotoxicity of 14 organic tin compounds (methyl-, butyl- and phenyltins) and inorganic tin (SnCU) on Escherichia coli and on Bacillus subtilis. Dibutyltin dichloride, tributyltin chloride, tributyltin chloride, bis(tributyl-tin)oxide, dimethyltin dichloride and trimethyltin chloride were all found to be genotoxic. 

Thain, J.E. and M.J. Waldock. 1986. The impact of tributyl tin (TBT) antifouling paints on molluscan fisheries. 

Walsh, G.E., L.L. McLaughlin, M K. Louie, C.H. Deans, and E.M. Lores. 1986b. Inhibition of arm regeneration by Ophioderma brevispina (Echinodermata, Ophiuroidea) by tributyl tin oxide and triphenyltin oxide. Ecotoxicol. Environ. Safety 12 95-100. 

Isomerization of bis(tributylstannyl)alkenyl compounds catalyzed by RuCl(H)(CO)(PPh3)3 gave the corresponding allylbis(tributyl)tin compounds in good yields (Scheme 51). These compounds are useful intermediates in organic synthesis.89... 

Tributyl tin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives led to highly functionalized cA-fused bicyclic ethers. The product could subsequently be transformed into optically active tricyclic nucleoside analogue or oxepine derivative (Fig. 51).67... 

Table 9.43 Enantioselective additions of alleny tributyl tin to aldehydes.

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