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 inOrganic letters Vol. 5; no. 4; pp. 575 - 578
Main Authors Langille, Neil F, Dakin, Les A, Panek, James S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.02.2003
Amer Chemical Soc
Subjects
Aldehydes - chemical synthesis
Chemistry
Chemistry, Organic
Hydrolysis
Indicators and Reagents
Ketones - chemical synthesis
Kinetics
Physical Sciences
Quinolizines
Science & Technology
Sulfides - chemistry
Sulfur Compounds
SECONDARY ALCOHOLS
OXIDATION
KETONES
1,3-DITHIANES
REAGENTS
CONVERSION
HYDROLYSIS
CARBONYL-COMPOUNDS
WATER
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ISSN1523-7060
1523-7052
DOI10.1021/ol027518n

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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.
Bibliography:Medline
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol027518n