Efficient Chemoselective Mild Deprotection of S,Sand S,O-Acetals and Ketals with Electrophilic Halogens

Author: Shaterian Hamid   Hadadzadeh Hassan  

Publisher: Taylor & Francis Ltd

ISSN: 1042-6507

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol.181, Iss.5, 2006-06, pp. : 1059-1071

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Abstract

A novel and simple method for the chemoselective deprotection of S , S - and S , O -acetals and ketals in the presence of their O , O -analogs with electrophilic halogens to their corresponding carbonyl compounds is described using N-bromosuccinimide, N-chlorosuccinimide, 2,4,4,6-tetrabromo-2,5-cyclohexen-1-one, trichlorocyanuric acid, or molecular bromine in aqueous acetonitrile. The use of these reagents in the presence of hydrated silica gel provide efficient, novel, and mild procedures for the deprotection of cyclic and acyclic O,O-, S,S-, and S,O-acetals and ketals in excellent yields in short reaction times.

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