Trimethyl tin chloride

The reaction of higher alkyl chlorides with tin metal at 235°C is not practical because of the thermal decomposition which occurs before the products can be removed from the reaction zone. The reaction temperature necessary for the formation of dimethyl tin dichloride can be lowered considerably by the use of certain catalysts. Quaternary ammonium and phosphonium iodides allow the reaction to proceed in good yield at 150—160°C (109). An improvement in the process involves the use of amine—stannic chloride complexes or mixtures of stannic chloride and a quaternary ammonium or phosphonium compound (110). Use of these catalysts is claimed to yield dimethyl tin dichloride containing less than 0.1 wt % trimethyl tin chloride. Catalyzed direct reactions under pressure are used commercially to manufacture dimethyl tin dichloride. 

Trimethvl Vinvlbenzvl Stannane—This procedure is identical to the preparation of trimethyl vinylbenzyl silane with the substitution of trimethyl tin chloride for the chlorotrimethyl silane. The following quantities were used 32.6 g (0.2136 mol) vinylbenzyl chloride in 65 mL of ether, 7.81 g (0.3211 mol) magnesium turnings. 

Two approaches for the synthesis of allyl(alkyl)- and allyl(aryl)tin halides are thermolysis of halo(alkyl)tin ethers derived from tertiary homoallylic alcohols, and transmetalation of other allylstannanes. For example, dibutyl(-2-propenyl)tin chloride has been prepared by healing dibutyl(di-2-propenyl)stannane with dibutyltin dichloride42, and by thermolysis of mixtures of 2,3-dimethyl-5-hexen-3-ol or 2-methyl-4-penten-2-ol and tetrabutyl-l,3-dichlorodistannox-ane39. Alternatively dibutyltin dichloride and (dibutyl)(dimethoxy)tin were mixed to provide (dibutyl)(methoxy)tin chloride which was heated with 2,2,3-trimethyl-5-hexen-3-ol40. 

Sodium dicyanoethylenedithiolate reacts with trimethyl- or triphenyl-tin chloride to give anionic trialkylstannadithiacyclopentenes, but dialkyltin dichlorides undergo dealkylation (231). 

A more detailed study (50) of the 119Sn chemical shifts of trimethyl-and triethyl-tin chloride as a function of concentration and temperature in various polar solvents has revealed the effect of complexing on chemical shift. The formation of a 1 1 complex of trialkyltin chloride in a polar donor solvent, L, may be written as ... 

To fight fire, use alcohol foam, CO2, dr) chemical. Violent polymerization occurs on contact with ammonia, alkali hydroxides, amines, metallic potassium, acids, covalent halides (e.g., aluminum chloride, iron(III) chloride, tin(IV) chloride, aluminum oxide, iron oxide, rust). Explosive reaction with glycerol at 200°. Rapid compression of the vapor with air causes explosions. Incompatible with bases, alcohols, air, m-nitroaniline, trimethyl amine, copper, iron chlorides, iron oxides, magnesium perchlorate, mercaptans, potassium, tin chlorides, contaminants, alkane thiols, bromoethane. When heated to... 

In their studies on the use of silyl-substituted ligands as thermal and oxidative stabilizers of transition metals, Pannell and collaborators [79] show that tram- -trimethylsilyl-3- / -allyl(trimethyl)tin can be prepared in an approximate 50% yield by the Barbier reaction of a trialkyl or triarylmetal chloride with magnesium metal and l-trimethylsilyl-3-chloroprop-l-ene. With nickel(II) chloride, magnesium, a trace of mercuric(ll) chloride, and 2-trimethylsilyl-3-chloroprop-l-ene, the thermally and oxidatively stable bis( / -2-trimethylsilylallyl)nickel derivative is prepared in 36% yield. The unsubstituted derivative is thermally unstable and ignites in air. 

In most cases the trimethyl tin reagents are preferred since the byproduct. trimethyltin chloride, can easily be removed by water extraction. In the case of the water-insoluble tributyltin chloride it is necessary to add an aqueous solution of potassium fluoride to an ethereal solution of the product thereby forming insoluble tributyltin fluoride, which can be separated by... 

Plastic pipes are polymeric in nature (e.g., polyvinyl chloride). Within the pipe are traces of the monomers used in the manufacture of the pipe (e.g., vinyl chloride). In addition, there are a variety of other chemicals added during the manufacture of the pipe as lubricants to facilitate their manufacture or stabilizers to prevent the breakdown of the pipe. In Europe, lead has been used as the stabilizer for pipes, whereas various organic tin compounds have been utilized in the United States. Lead is widely recognized as being toxic. Inorganic tin has a very limited toxicity, but this is not the form of tin that is used. Some of the organic tin compounds are potent nervous system toxins (e.g., trimethyl or triethyl tin), while others appear to adversely affect the immune system (dioctyl tin). The forms of tin used in polyvinyl chloride pipe, however, are primarily monomethyl and dimethyl tin, which are much less active as neurotoxins than the trimethyl tin. There will be some extraction of all these chemicals from the pipe when it is first put into service. However, the concentrations that are found in the water decrease sharply with continued use of the pipe. This is only partially due to the depletion of the chemical from the pipe because continuous water flow will form an impermeable barrier (e.g., calcium carbonate) on the interior of the pipe that minimizes leaching from its surface. 

Optically active 2-allylpiperidines and -pyrrolidines arc obtained by treating hydroxylactams containing the l-[(S)-l-arylethyl]substituent as an auxiliary (see Appendix) with tin(IV) chloride and trimethyl(2-propenyl)silane46. Interestingly, the moderate diastereoselection when the aryl group is phenyl decreases when 2-chlorophenyl is used, whereas the sense of the stereoselectivity reverses for 2,6-dichlorophenyl or pentachlorophcnyl. These results are rationalized by application of molecular orbital theory and substrate conformational preferences46. 

Inductively coupled plasma mass spectrometry was applied to the analysis of six organotin compounds (chlorides of dimethyl-, dibutyl-, trimethyl-, tributyl-, diphenyl-, and triphenyltin). Detection hmits for the six organotins ranged from 24 to 51 pg as tin the dynamic range was over lO, from 1 pg/1 to 10 mg/1 (Inoue Kawabata, 1993). 

Azine approach. The fused uracil (58) has been prepared from 5-amino-l,3,6-trimethyl-uracil diazotization of the latter yields a fused triazine A-oxide (57), which has its triazine ring transformed into an isoxazole ring by tin(II) chloride treatment (62USP3056781). 

A mixture of 6-bromo-4-(tri luoromethanesulfonyloxy)-5,8-dimethoxy-quinoline (1.35 g, 3.25 mmol), trimethyl[2-[(l,l-dimethylethoxycarbonyl)-amino]phenyl]tin (1.68 g, 4.70 mmol), lithium chloride (330 mg, 7.80 mmol), copper(I) bromide (25 mg, 0.17 mmol), and tetrakis(triphenylphosphine)palla-dium (0) (180 mg, 0.16 mmol) in dioxane (60 cm ) was heated at 90 °C for 60 h. After being cooled to rt, the mixture was partitioned between EtOAc and a 5 % aqueous ethylenediamine solution to remove any copper species, completely. After the usual work up, the residue was chromatographed (1.5 1 hexanes -EtOAc) to yield the title compound as a white solid (952 mg, 64%, several other fractions contained the title compound contaminated with 6-bromo-5,8-di-methoxy-4-methylquinoline) mp 166-168 °C. 

Tin trimethyl chloride may be formed from the hydroxide by the action of hydrochloric acid. It has more recently been obtained Irom tin trimethyl solutions by the action of calcium chloride in dry air, and by treating tin trimethyl with mercuric chloride in ethereal solution. It is a liquid having similar properties to the ethyl compound. It forms a compound with 1 mol. of aniline, and with 1 mol. of pyridine, the latter melting at 37 C. By reduction with sodium in liquid ammonia it yields sodium trimethyl stamnide which is a light yellow substance readily decomposing above the temperature of liquid ammonia. It reacts with tin trimethyl halides to give tin trimethyl. The electrical conductivity of tin trimethyl chloride in absolute alcohol at 25 C. has been determined.- ... 

Tin trimethyl hydroxide is isolated from the iodide by action of potassium hydroxide. It crystallises in prisms and is volatile iii steam. The aqueous solution is strongly alkaline, and the solubility in alcohol is greater than in water. With tin trimethyl halides it forms complexes of the type (Me jSnOH)2.Me jSnX, the bromide melting at 113° to 115° C. with decomposition iodide 143° to 153° C. with decomposition also the type Me SnOH.MejjSnX.HgO, the chloride M.pt. 90° C. bromide, M.pt. 210° to 211° C. with decomposition iodide, M.pt. 221° C. with decomposition. The electrical conductivity of solutions of the hydroxide has been determined by Bredig.-... 

Tin trimethyl benzyl is prepared from sodium trimethyl stannide and benzyl chloride in liquid ammonia, according to the equation ... 

Five coordinate germanium(IV) complexes l,l,5-trimethyl-2,8-dioxa-5-aza-l-germa-bicyclo [3.3.01,5]octane diones (163) can be prepared from the reaction of R2GeX2 (R = Me, Ph X = C1, OR) with MeN(CH2C02H)2." Tridentate ligand 5-aza-2,2,8,8-tetramethylnonane-3,7-dione reacts with tin(IV) chloride to form (164), comprising a tin(II) center which is liable to oxidation by SO2CI2 to form (165)." ... 

Trimethyl((V-phenylbenzimidoyl)stannane reacts with halides such as benzyl or allyl bromide, benzoyl chloride, or methyl iodide in the presence of KF and 18-crown-6 to give the corresponding ketimine presumably attack of the fluoride ion at tin gives an imidoyl anion equivalent73... 

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