Triphenylmethanol, formation

Triphenylmethanol is a tertiary alcohol and undergoes, as expected, SnI reactions. The intermediate cation, however, is stable enough to be seen in sulfuric acid solution as a red-brown to yellow solution. Upon dissolution in concentrated sulfuric acid, the hydroxyl is protonated then the portion is lost as HjO (which is itself protonated) leaving the carbocation. The bisulfate ion is a very weak nucleophile and does not compete with methanol in the formation of the product, trityl methyl ether. 

O-Tritylcellulose, 5 This polymer gave satisfactory elemental analyses, and showed no apparent loss in DPw upon formation (Table 1). When doped with 5% by weight triphenylmethyl compounds (triphenylmethane and triphenylmethanol) or left unpurified from the reaction mixture, it formed films from methylene chloride. These exhibited Tg at 126.7 °C (by DMA) and modulus (E ) of 3.26 GPa at 20 C. The material degraded at 308 C by TGA. Polymer 5, when pure, did not provide useful films for DMA analysis. 

Heating 1,1,1-triphenylmethanol with ethanol containing a trace ofa strong acid causes the formation of 1-ethoxy-1,1,1-triphenylmethane. Write a plausible mechanism that accounts for the formation of this product. 

Triphenylmethanol treated with 0.55 eqs. of Lawesson s reagent in DME at room temp, under argon for 15 h (or in toluene under reflux for ca. 10 min) triphenyl-methanethiol. Y 100%. Reaction of tert. alcohols possessing an alkyl group at the a-position led to alkene formation (especially in refluxing toluene), but thiol formation predominated at lower temp. F.e. [of sec. and tert. benzylic or allylic mercaptans] s. T. Nishio, J. Chem. Soc. Chem. Commun. 1989, 205-6. 

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