A Mild, Chemoselective Protocol for the Removal of Thioketals and Thioacetals Mediated by Dess−Martin Periodinane

This paper describes the development of a useful procedure for the removal of thioacetals and thioketals using Dess−Martin periodinane (DMP) reagent. In contrast to existing methods, this protocol offers general reactivity, compatibility with a wide range of functional groups, and convenient reactio...

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Bibliographic Details
Published in:Organic letters 2003-02, Vol.5 (4), p.575-578
Main Authors: Langille, Neil F, Dakin, Les A, Panek, James S
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Hydrolysis
Indicators and Reagents
Ketones - chemical synthesis
Kinetics
Quinolizines
Sulfides - chemistry
Sulfur Compounds
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Summary:This paper describes the development of a useful procedure for the removal of thioacetals and thioketals using Dess−Martin periodinane (DMP) reagent. In contrast to existing methods, this protocol offers general reactivity, compatibility with a wide range of functional groups, and convenient reaction times. Also discussed are chemoselectivity experiments involving functionalities that may be subject to oxidation by DMP, qualitative effects of substrate on hydrolysis rate, and direct thioacetal to acetal conversions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027518n