Tricyclohexyltin chloride

Tricyclohexyltin chloride is converted to the hydroxide with sodium hydroxide. The tria2ole can be prepared from the chloride with sodium or potassium hydroxide and l,2,4-tria2ole. 

The structural chemistry of the organotin halides is dominated by their Lewis acid properties and their propensity to form five- and six-coordinate complexes. Self-association may give oligomers or polymers in the solid state, which usually dissociate in solution. The structure of tricyclohexyltin chloride in the crystal is temperature-dependent. At 108 K, it has the form of a rod-like polymer with distorted trigonal-bipyramidal tin and Sn-Cl separations of 245.6(7) and 300.77(7) pm, but at 298 K, the structure is best regarded as consisting of near-tetrahedral discrete molecules.3... 

Hlsdricyclohexyltin) sulfide-Boron trichloride. The sulfide (1), m.p. 132°, is prepared by reaction of tricyclohexyltin chloride with Na,S 9H,0 in refluxing ethanol. 

Scheme 3.7.1 Coupling of Grignard reagents with tricyclohexyltin chloride...

The reaction of o, y-dibromomagnesioalkanes with tricyclohexyltin chloride leads to the expected ditins 62, 65, 67, and 70, separated by up to 10 methylene groups in high yields (Scheme 3.7.10).22... 

It is facile to prepare dibenzyl derivatives, such as 78, when the corresponding Grignard reagents are stable. However, when they are not, because of the occurrence of an intensive polycondensation of the dihalide in spite of high dilution conditions, Barbier conditions prove to be very efficient (Scheme 3.7.12). The simultaneous reaction of l,4-bis(chloromethyl)benzene or 4,4 -bis(chloromethyl)biphenyl with tricyclohexyltin chloride and magnesium allows the preparation of -substituted dibenzyl derivatives 81 and 84, with one or two phenyl rings. 

Then, when the hexacyclohexylorganoditins are treated with one equivalent of tin tetrachloride, the corresponding trichlorides are recovered in high yield, after extraction of tricyclohexyltin chloride from the reaction mixture with pentane (Scheme 3.7.16). In the case of hexamethylorganoditins, an excess of tin tetrachloride is necessary to obtain the corresponding hexachlorides, 100 and 105, and no decomposition of the expected organoditin hexachlorides occurs during the distillation of the mixture of methyltin chlorides formed. 

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)...

Some other triorganotin monochlorides are not associated in the solid state. Tri-phenyltin monochloride (Sn-Cl 2.353 A) [186] was described as discrete unassociated in the solid state and even tricyclohexyltin chloride was first described as monomeric [187], like the triorganotin bromides and iodide investigated so far (see Table 4.1). Tris(m-tolyl)tin chloride (Sn-Cl 2.379 A) and tris(3,5-dimethylphenyl)tin chloride (Sn-Cl 2.357 A) are also discrete monomers [187a]. 

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