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Synthesis 2009(8): 1393-1399  
DOI: 10.1055/s-0028-1088023
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Mild Deprotection Protocol for 1,3-Dithianes and 1,3-Dithiolanes with 30% Hydrogen Peroxide and Iodine Catalyst in Aqueous Micellar System

Nemai C. Ganguly*, Sujoy Kumar Barik
Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
Fax: +91(33)25828282; e-Mail: nemai_g@yahoo.co.in;
Further Information

Publication History

Received 3 December 2008
Publication Date:
25 March 2009 (online)

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Abstract

A simple clean expeditious protocol for the deprotection of 1,3-dithianes and 1,3-dithiolanes has been developed using 30% aqueous hydrogen peroxide activated by iodine catalyst (5 mol%) in water in the presence of sodium dodecyl sulfate (SDS) under essentially neutral conditions. The method showed tolerance for a number of phenol protecting groups such as allyl, benzyl, TBDMS, TBDPS ethers, phenolic acetates, and benzoates as well as amino-protecting BOC, Cbz carbamates without any detectable overoxidation.

Key words

1,3-dithianes - 1,3-dithiolanes - iodine - 30% hydrogen peroxide - sodium dodecyl sulfate (SDS)

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