Reactions of caesium fluoroxysulphate with organic molecules Part 25. Reactions with ethers

Abstract

The reactions of caesium fluoroxysulphate in MeCN suspension at room temperature with di-benzyl, di-alkyl or benzyl-alkyl ethers resulted in oxidative cleavage of the ethers forming pairs of corresponding aldehydes and alcohols, which could be further transformed into acid fluorides under the reaction conditions used. Di-benzyl ether was thus transformed to a mixture of benzyl alcohol, benzaldehyde and benzoyl fluoride as the main products and benzyl benzoate as the a minor one, while di-n-hexyl ether resulted in a mixture of n-hexanol, hexanal, hexanoyl fluoride and hexyl hexanoate. The reaction of benzyl hexyl ether resulted in a mixture of benzaldehyde, benzoyl fluoride and hexanol as the main, and benzyl alcohol, hexanal, hexanoyl fluoride and hexyl benzoate as the minor products. A reaction mechanism including radical intermediates was proposed.