A mild, chemoselective protocol for the removal of thioketals and thioacetals mediated by Dess-Martin periodinane.
[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.
Langille
Neil F
NF
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.
Dakin
Les A
LA
Panek
James S
JS
D000447:Aldehydes / Q000138:chemical synthesis*; D006868:Hydrolysis; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis*; D007700:Kinetics; D011807:Quinolizines; D013440:Sulfides / Q000737:chemistry*; D013457:Sulfur Compounds
D000447:Aldehydes; D007202:Indicators and Reagents; D007659:Ketones; D011807:Quinolizines; D013440:Sulfides; D013457:Sulfur Compounds; C438055:dithiane