Mild and Eco-friendly oXidative Cleavage of 1,3-dithianes and 1,3-dithiolanes with a Catalytic Amount of Hydrobromic Acid and Hydrogen Peroxide: Synergetic Effect of Bromonium Ion Equivalent and Hydrogen Peroxide
Free accessResearch articleFirst published online April, 2005
Mild and Eco-friendly oXidative Cleavage of 1,3-dithianes and 1,3-dithiolanes with a Catalytic Amount of Hydrobromic Acid and Hydrogen Peroxide: Synergetic Effect of Bromonium Ion Equivalent and Hydrogen Peroxide
A combination of a catalytic amount hydrobromic acid (10 mol%) and an excess of hydrogen peroxide is found to be an effective reagent for expeditious regeneration of carbonyl compounds from their 1,3-dithiane as well as 1,3–dithiolane derivatives. Absence of nuclear bromination of aromatic substrates and overoxidation of regenerated oxidation–prone aromatic aldehydes, compatibility with a number of functional groups, such as amino, hydroxy, acetoxy, methylenedioxy and useful phenol-protecting allyl, benzyl and TBDMS ethers, benzoate esters and amino-protecting Cbz carbamate and N-benzylamine (NHBn) moieties are the advantageous features of this protocol.
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