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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
It is applied in the abstraction of the ɑ-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 ɑ-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.
Solubility
Insoluble in water. Soluble in methanol.
Notes
Moisture sensitive. Store away from bases, water/moisture, heat and oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Store under inert gas. Keep it refrigerated.
RUO – Research Use Only
General References:
- 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).