Butyltin chlorides

Pechiney (2002) Tin chemicals — mono butyltin chloride. Pechiney UK Limited (http //www.pechiney.co.uk accessed 2003). 

Hodge et al. [92] have described an atomic absorption spectroscopic method for the determination of butyltin chlorides and inorganic tin in natural waters, coastal sediments, and macro algae in amounts down to 0.4 ng. 

An estimate of the accuracy of both analytical methods was performed on bis(tri-n-butyltin) oxide and tri-n-butyltin chloride solutions (8.9-35.6 ig/l) prepared in filtered (0.45 im) near-shore seawater free of detectable organ-otins. Average mean recoveries of 92.8% by both methods were determined for tributyltin standard solutions. Low ng/1 levels of mono-, di-, and tributyltin were found in samples taken from San Diego Bay. 

Reader, S., H.B. Steen, and F. Denizeau. 1994. Intracellular calcium and pH alterations induced by tri-n-butyltin chloride in isolated rainbow trout hepatocytes a flow cytometric analysis. Arch. Biochem. Biophys. 312 407-113. 

Tsuda, T., S. Aoki, M. Kojima, and T. Fujita. 1992. Accumulation and excretion of Iri-n-butyltin chloride and triphenyltin chloride by willow shiner. Comp. Biochem. Physiol. 101C 67-70. 

Tsuda, T., S. Aoki, M. Kojima, and H. Harada. 1991. Accumulation of Iri-n-butyltin chloride and triphenyltin chloride by oral and via gill intake of goldhsh (Carassius auratus). Comp. Biochem. Physiol. 99C 69-72. Tsuda, T., H. Nakanishi, S. Aoki, and J. Takebayashi. 1986. Bioconcentration of butyltin compounds by round Crucian carp. Toxicol. Environ. Chem. 12 137-143. 

The most widely used, and often most convenient reagents for such one-pot reactions are sodium hypochlorite (45) or hypobromite (16). These reactions are performed in the presence of an organic base (generally triethylamine) that normally enhances the yield of cycloaddition products (45). This method was employed for many intermolecular reactions (71) and also seems especially suited for intramolecular ones (72-77) as well as for the solid-phase synthesis (78) of 2-isoxazolines. Hypohalite can also be replaced by sodium broruite in combination with a catalytic amount of tri-u-butyltin chloride (79). In a related method, O-tributylstannyl oximes were treated with tert-butyl hypochlorite to produce nitrile oxides that were trapped with aUcenes or alkynes to afford the corresponding isoxazolines or isoxazoles in moderate to good yield (80). 

Figure 6.12 The cellular toxicity of TBT caused by damage to the thiols of the Ca2+ pump. This leads to dramatic mobilization of calcium from the ER. The filled circles represent ATP-dependent Ca2+ transporters. Abbreviations TBT, tri-n-butyltin chloride ER, endoplasmic reticulum.

J. T. Groves, S. Kittisopikul, Dehalogenation reactions catalyzed by tri-n-butyltin chloride. Competition for carbon radicals by borohydride and tin hydride. Tetrahedron Lett. 49 429I (1977). 

In a fume hood, 19.2 g. (0.059 mole) of tri-n-butyltin chloride and then 140 ml. of ethylene glycol dimethyl ether (monoglyme) which has been purified by distillation from calcium hydride at atmospheric pressure on an efficient fractionating column (fraction used boils at 85 1°C.) are added to a pressure-equalized 250-ml. dropping funnel, and the funnel gently agitated to dissolve all the tributyltin chloride. 

The IR spectrum in Nujol of l,2,4-thiadiazolidine-3,5-dithione indicates that the dithione structure (18a) predominates. However, the dithione can be readily dialkylated on sulfur. Thus, treatment with 2,3-dichloropropene in aqueous sodium hydroxide forms (208 Scheme 73) (65AHC(5)119). The disulfenamide (209) condenses with aldehydes and ketones to give the corresponding imines (210) and (211 Scheme 74) (74ZOB2553). 5-Mercapto-3-methyl-thio-l,2,4-thiadiazole (212) reacts with di- -butyltin chloride in THF to give di-n-butyltin derivative (213 Scheme 75) (72USP3634442). 

In the initial studies about the reaction of /V.zV-disubstituted formamides with alkaline metals to give glyoxylic amides, the participation of carbamoyl metal derivatives as intermediates was postulated83. The first preparation of the carbamoyllithium 77 was described two years later by a mercury-lithium transmetallation from compound 76 at —75 °C (Scheme 20)84. The authors proposed also an aminocarbene structure 78 and studied its reactivity with methanol, methyl iodide, carbonyl compounds, esters, acyl chlorides, mercury(II) chloride and tri-n-butyltin chloride providing compounds 79. 

Palladium-catalyzed hydrostannylation is stereoselective, giving syn-adduct. Regioselectivity is not always perfect, however. Exclusive formation of (-B)-l-stannylalkene is obtained only when 1-alkyne with a bulky substituent is employed (Scheme 34) [147-150]. Nicolaou also reported a stereo- and regio-selective hydrostannylation (Scheme 35) [151]. Use of a combination of tri-butyltin chloride and poly(methylhydro)siloxane in the presence of TBAF is also an impressive method in this class [152]. 

Prepared by reaction of tri-n-butyltin chloride with triflic acid. 

Fluorinated aUcyl vinyl and aryl cadmium reagents can be prepared in excellent yields just by stirring the fluorinated halides with activated cadmium metal. These reagents can then be used to prepare the corresponding fluorinated stan-nanes, which are versatile synthetic intermediate, by reacting them with tri-n-butyltin chloride at room temperature. Similar methods have been used to synthesize fluorinated copper reagents. ... 

SYNS CHLORID TRI-n-BUTYLCINICITY (CZECH) TRIBUTYLCHLOROSTANNANE TRI-n-BUTYLTIN CHLORIDE TRI-n-BUTYLZINN-CHLORID (GERMAN)... 

Preparation. The reagent is prepared in 81% yield by the reaction of tri-n-butyltin chloride (Metal and Thermit Corporation) with CH2=CHCH2CH2MgBr. 

J. T. Groves, S. Kittisopikul, Dehalogenation reactions catalyzed by tri-n-butyltin chloride. Competition for carbon radicals by borohydride and tin hydride, Tetrahedron Lett. 49 4291 (1977). N. M. Weinshenker, G. A. Crosby, and J. Y. Wong, Polymeric Reagents. IV. Synthesis and utilization of an insoluble polymeric organotin dihydride reagent, J. Org. Chem. 40 1966 (1975). 

Table 4.5.1 Effects of tri-n-butyltin chloride on the lytic function, binding function, ATP levels, CD16 levels, CD56 levels, granzyme B levels, and perforin levels of human NK cells ...

Effects of n-butyltin Chlorides on Human NK Cell Function Tri-n-Butyltin Chloride (TBTC)... 

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