Oxidative Deprotection of Trimethylsilyl Ethers to the Corresponding Carbonyl Compounds Using Cetyltrimethylammonium Peroxodisulfate

Abstract

Cetyltrimethylammonium peroxodisulfate (CTA)₂S₂O₈ was quantitatively prepared and used for the oxidation and deprotection of trimethylsilyl ethers to the corresponding carbonyl compounds in acetonitrile. Selective oxidation of allylic or benzylic trimethylsilyl ethers in the presence of saturated alkyl trimethylsilyl ethers were also achieved. This new reagent is more efficient and has several advantages over similar oxidants in terms of the amount of oxidant, short reaction time, simple work up, and high yield.

Keywords:

• Cetyltrimethylammonium peroxodisulfate
• deprotection
• oxidation
• trimethylsilyl ethers

Acknowledgments

Financial support from the Research Council of Mazandaran University is gratefully acknowledged.

Notes

^a Yields refer to isolated products.

^a Products were characterized by their physical constants, spectroscopic data (IR, ¹H NMR), GC, and comparison with authentic samples;

^b yield of isolated pure carbonyl compounds.

^aYield was determined by ¹H NMR.

^a 2,6-Dicarboxypyridinium fluorochromate;

^b quinolinium fluorochromate;

^c 3-carboxypyridinium chlorochromate;

^d benzyltriphenylphosphonium peroxodisulfate; and

^e allyltriphenylphosphonium peroxodisulfate.