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It is applied in the abstraction of the ?-H atom of alcohols and their O-substituted derivatives results in oxidation to the ketones and in the oxidation of TMS ethers to ketones, secondary alcohols to ketones, and secondary diols to ?-hydroxy ketones. It is applied as a reactant involved in the synthesis of substituted dihydroazulene photo switches, carbene-based Lewis pairs for hydrogen activation, 1,3-Dipolar cycloaddition reactions for preparation of α-amino-β-hydroxy esters, oxidation of allenic compounds, Mukaiyama aldol addition reactions and ionic hydrogenation as a counteranion and ligand source.
Louise Skov, et al. New synthetic route to substituted dihydroazulene photoswitches.Org Biomol Chem.,2011,9(19), 6498-6501.
J. Danielsson, et al. 1,3-Dipolar Cycloaddition of Azomethine Ylides to Aldehydes: Synthesis of anti a-Amino-ß-Hydroxy Esters.European J. Org. Chem.,2011,3607-613.
T. Yamaguchi, et al. Demethylation of an Allene Bearing Two Dimethoxythioxanthene Groups by Oxidation via a Vinyl Cation Intermediate.Aust. J. Chem.,2010,631638-1644.
The trityl cation abstracts hydride ion from a variety of substrates:
Cycloheptatriene gives the tropylium cation: J. Am. Chem. Soc., 79, 4557 (1957).
With 1,3-Dithiane, A10505, gives the electrophilic dithienium salt which can react with silyl enol ethers to give ɑ-formyl or ɑ-methyl carbonyl compounds: Tetrahedron Lett., 22, 2829, 2833 (1981).
Abstraction of the ɑ-H atom of alcohols and their O-substituted derivatives results in oxidation to the ketones:
Oxidation of TMS ethers to ketones: J. Org. Chem., 41, 1479 (1976); secondary alcohols to ketones, and secondary diols to ɑ-hydroxy ketones: Tetrahedron Lett., 2771 (1978). Ketones can similarly be oxidized to ɑß-unsaturated ketones by hydride abstraction from their silyl enol ethers: J. Org. Chem., 42, 3961 (1977); Synthesis, 736 (1979).
The trityl cation is also useful for the oxidative cleavage of the 4-methoxybenzyl protecting group from secondary alcohols: J. Org. Chem., 49, 51 (1984).
Hazard Statements: H314-H318
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