A mild,chemoselective protocol for the removal of thioketals and thioacetals mediated by Dess-Martin periodinane |
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| Authors: | Langille Neil F Dakin Les A Panek James S |
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| Affiliation: | Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA. |
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| Abstract: | [reaction: see text] 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. |
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