Efficient and Selective Oxidative Deprotection of Tetrahydropyranyl Ethers, Ethylene Acetals and Ketals with Silver and Sodium Bromates in the Presence of Aluminum Chloride

Iraj Mohammadpoor-Baltork; Ali Reza Nourozi

doi:10.1055/s-1999-3410

Synthesis 1999; 1999(3): 487-490
DOI: 10.1055/s-1999-3410

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Efficient and Selective Oxidative Deprotection of Tetrahydropyranyl Ethers, Ethylene Acetals and Ketals with Silver and Sodium Bromates in the Presence of Aluminum Chloride

Iraj Mohammadpoor-Baltork^* , Ali Reza Nourozi

^*Chemistry Department, Esfahan University, Esfahan, 81744, Iran; Fax +98(31)68 73 96

Abstract

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Primary and secondary tetrahydropyranyl (THP) ethers are efficiently transformed to their carbonyl compounds with AgBrO₃ and NaBrO₃/AlCl₃. Ethylene acetals and ketals are transformed to their carboxylic acids and ketones respectively with AgBrO₃/AlCl₃ in refluxing acetonitrile. AgBrO₃/AlCl₃ is also able to transform ethylene acetals to aldehydes in refluxing carbon tetrachloride in high yields. In refluxing acetonitrile, ethylene acetals and ketals are transformed to aldehydes and ketones with NaBrO₃/AlCl₃. We have also found that tetrahydropyranyl ethers are oxidized selectively in the presence of ethylene acetals and ketals with these reagents.

tetrahydropyranyl ethers - acetals - ketals - oxidative deprotection - bromates

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