Triphenyl methyl chloride

Triphenylmethyl thioethers have been formed by reaction of the thiol with tri-phenylmethyl alcohol/anhydrous CF3COOH (85-90% yield) or with triphenyl-methyl chloride (75% yield). 

Two pieces of direct evidence support the manifestly plausible view that these polymerizations are propagated through the action of car-bonium ion centers. Eley and Richards have shown that triphenyl-methyl chloride is a catalyst for the polymerization of vinyl ethers in m-cresol, in which the catalyst ionizes to yield the triphenylcarbonium ion (C6H5)3C+. Secondly, A. G. Evans and Hamann showed that l,l -diphenylethylene develops an absorption band at 4340 A in the presence of boron trifluoride (and adventitious moisture) or of stannic chloride and hydrogen chloride. This band is characteristic of both the triphenylcarbonium ion and the diphenylmethylcarbonium ion. While similar observations on polymerizable monomers are precluded by intervention of polymerization before a sufficient concentration may be reached, similar ions should certainly be expected to form under the same conditions in styrene, and in certain other monomers also. In analogy with free radical polymerizations, the essential chain-propagating step may therefore be assumed to consist in the addition of monomer to a carbonium ion... 

The reverse reaction of triphenyl methyl chloride (A) and methanol (B) (C6H5)3CC1 + CH3OH (C6H5)3COCH3 + HC1... 

MeOH or eth. It was prepd by the interaction of triphenyl methyl chloride and Na azido-dithiocarbonate in acet. The ppt was recrystd from chlf... 

It is instructive to compare a C-metal bond with e. g. a C-Cl bond. The carbon chlorine bond exists in two forms as a covalent C-Cl and as an ion pair C+, Cl-. The equilibrium between these two forms in compounds such as triphenyl methyl chloride was studied e.g. by A. G. Evans... 

In ionic polymerization a hydride (H-) transfer or a proton transfer are the analogues of the hydrogen atom transfer in radical polymerization. A hydride (H-) ion transfer is observed in many isomerizations and dimerizations of hydrocarbons which proceed via carbonium-ion mechanism. A similar process is responsible for chain transfer ip some carbonium-ion polymerizations. The transfer of negative ions like Cl- is also common, e.g. triphenyl methyl chloride is an efficient transfer agent in such a polymerization. Transfer of a proton is, on the other hand, a very common mode of termination of anionic polymerization. Indeed, this mode of termination was discussed previously in connection with branching reactions, and it was postulated in the earliest studies of anionic poly-... 

Evans, A. G., et al. Ionization of triphenyl methyl chloride with nitroalkanes. Trans. Faraday Soc. 47, 711 (1951). 

The resultant tetra-methyl-diamino-triphenyl methane is then oxidised to the carbinol, which is converted to malachite green by hydrogen chloride ... 

Triphenyl methyl chloride in benzene solution reacts with an ether solution of RMgCl thus 7 (CgHj)3C.C1 + RMgCl = (CGH5)aC.R + MgCL Hydrocarbons are formed by the action of methyl sulphate upon RMgX ... 

Easily dissociable, highly polar organic compounds were used occasionally as cationic initiators. Thus, triphenyl methyl chloride (77), triphenyl methyl chloromercurate (72), alkyl, acyl, and nitronium tetra-fluoro borates (13), silver perchlorate (77, 14), lithium perchlorate (75), acetyl, benzoyl, and tert.-butyl perchlorate (16) and acetyl fluoroborate (16) were mentioned at various times as catalysts for cationically initiable monomers. 

Here the reaction shows mass-law inhibition by one of its products X, while the concentration of carbonium ion R+ is at its equilibrium value. One would expect such limiting behavior only in very exceptional cases, since it would imply reaction in a reasonably strongly ionizing solvent at low water content. Very few cases have been observed to fit this limiting behavior, but one example is provided by the hydrolysis of triphenyl methyl chloride in 85 per cent aqueous acetone. The apparent first-order rate constant for hydrolysis is decreased fourfold by 0.01 M NaCl and remains unchanged on the addition of other salts, such as NaC104, not having the common Cl ion. "... 

Velichkova et al. studied the photolyses of various trityl salts ( 10 M in CH2CI2) by visible light and identified a number of products including triphenylmethane, fluo-renone and phenylfluorenones. With anions containing chlorine, e.g. SbCl, triphenyl-methyl chloride was a major product. 

Part (1) Detemitie the reaction order with respect to triphenyl methyl chloride. Part (2) In a separate set of experiments, the reaction order wrt methanol was found to be first order. Determine the specific reaction rate constant. 

Look for simplifications. Because concentration of methanol is 10 times the initial concentration of triphenyl methyl chloride, its concentration is essentially constant... 

Use the integral method to confirm that the reaction is second order wrt triphenyl methyl chloride as described in Example 5-1 and to calculate the specific reaction rate k ... 

Reactions of Isoxazoles. The kinetics of the isoxazole azirine rearrangement (336) -> (337) and those of the isoxazole oxazole transformation (338) (339) have been determinedPalladium(II) chloride-triphenyl-phosphine catalyses the cross-coupling of 4-iodo-3,5-dimethylisoxazole with styrene to yield the trans- compound (340). 3,5-Dimethylisoxazole can be lithiated in two stages, first at the 5-methyl group and then at the 3-methyl group. Isoxazoles add hypochlorous acid to form 4-chloro-2,3-dihydro-... 

Solution-Phase Ionization of Tropenyl Chloride and Triphenyl-methyl Chloride. Insofar as thermal degradation is concerned, the critical phase in PVC processing occurs in the melt, which may reach temperatures in the vicinity of 200°C (73) over a period of some minutes. The dielectric constant of PVC (3-4 at 25°C, 11-12 at 140°C) (74) is comparable with that of small chlorocarbons (75). Of the organic chlorides whose ionization has been studied in such solvents, tropenyl chloride and triphenylmethyl chloride seem to have received the most attention. 

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