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New methods for peroxide synthesis
Abstract
Three new methods have been developed for the synthesis of organic peroxides. The reagent 2-methoxyprop-2-yl hydroperoxide is used as an efficient alternative to anhydrous hydrogen peroxide for the synthesis of alkyl hydroperoxides and peracids. Wittig or Horner-Wadsworth-Emmons olefination of aldehydes containing a ketalized hydroperoxide is used as a new method for the synthesis of unsaturated hydroperoxides. Finally, an asymmetric synthesis of hydroxy endoperoxides has been developed based upon chemoselective addition of organometallic reagents to a protected version of 4(S)-hydroperoxy-2(E)-nonenal. Oxidation of the resultant allylic alcohol to the 4-peroxy-2-enone, followed by photochemical isomerization of the corresponding hydroperoxyenone, produces the cyclized peroxide, a 3-hydroxy-3-dioxin.
Subject Area
Organic chemistry
Recommended Citation
Sahli, Ayman, "New methods for peroxide synthesis" (1994). ETD collection for University of Nebraska-Lincoln. AAI9425308.
https://digitalcommons.unl.edu/dissertations/AAI9425308