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• W106711616 endingPage "1086" @default.
• W106711616 startingPage "1077" @default.
• W106711616 abstract "It has been widely accepted that both the protection of carbonyls and the deprotection of acetals and ketals involve the participation of a water molecule: formation of acetals and ketals is a dehydration process, whereas the deprotection is often referred to as hydrolysis, which, as implied by its name, always requires the presence of water. Herein, we report experimental evidence and mechanistic investigations that provide an alternative view to this process. We have demonstrated that water is not required to convert acetals and ketals to the corresponding carbonyls. The 1H NMR experimental results revealed that the TFA-mediated transformation of acetal to aldehyde occurs via a hemiacetal TFA ester intermediate, which differentiates itself from the classic acid-catalyzed hydrolysis, where the hemiacetal is the putative intermediate responsible for the formation of the aldehyde. More interestingly, alcohols are not the final byproducts as they are in the classical hydrolysis, rather, the two alcohol molecules are converted to two TFA esters under the reaction conditions. On the basis of the NMR evidence, we have proposed that the two TFA esters are formed in two separate steps via a different mechanism along the reaction pathway. Formation of the TFA esters renders the reaction irreversible. To the best of our knowledge, the cascade reaction pathway presented by the TFA-mediated conversion of acetals and ketals to carbonyls has never been previously postulated." @default.
• W106711616 created "2016-06-24" @default.
• W106711616 creator A5000432967 @default.
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• W106711616 creator A5071371875 @default.
• W106711616 creator A5085975474 @default.
• W106711616 date "2010-01-22" @default.
• W106711616 modified "2023-10-16" @default.
• W106711616 title "Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions" @default.
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• W106711616 doi "https://doi.org/10.1021/jo902014z" @default.
• W106711616 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/20095540" @default.
• W106711616 hasPublicationYear "2010" @default.
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