Removal of Thioacetal Protecting Groups by Cerium (IV) Ammonium Nitrate - Hydrolysis of 1,3-Dithiannes

Autor:	Henri-Jean Cristau, Henri Christol, Bernard Chabaud, Richard Labaudinière
Rok vydání:	1981
Předmět:	Chemistry Ammonium nitrate Organic Chemistry Inorganic chemistry Thioacetal chemistry.chemical_element Umpolung Mercury (element) Metal chemistry.chemical_compound Hydrolysis Cerium visual_art visual_art.visual_art_medium Organic chemistry
Zdroj:	Synthetic Communications. 11:423-428
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397918108061872
Popis:	In the course of our work on umpolung of α,β-ethylenic ketones and aldehydes1, the use of thioacetalised γ-ketophosphonium salts and ylids led us to investigate the hydrolysis of 1,3-dithianes. Among the known methods of removal of thioacetal protecting groups2, the one using cerium (IV) ammonium nitrate (CAN) has the advantages of a fast reaction with easy work-up and good to very good yields3. This method has been widely applied for preparative purposes using four equivalents of the cerium salt. However it does not seem that a theoretical explanation has been brought for the use of such a quantity of CAN. The only one proposed4 deals with a mechanism similar to the one involving mercury (II) salts, where indeed, four equivalents of metallic salt are not necessary5.
Databáze:	OpenAIRE
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