Related Experiment Video
Updated: Jan 4, 2026

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
Published on: April 2, 2018
Oxodealkenylative Cleavage of Alkene C(sp3 )-C(sp2 ) Bonds: A Practical Method for Introducing Carbonyls into Chiral
Andrew J Smaligo1, Jason Wu1, Nikolas R Burton1
1Department of Chemistry & Biochemistry, University of California-Los Angeles, Los Angeles, CA, 90095-1569, USA.
Abstract:
Reported herein is a one-pot protocol for the oxodealkenylative introduction of carbonyl functionalities into terpenes and terpene-derived compounds. This transformation proceeds by Criegee ozonolysis of an alkene, reductive cleavage of the resulting α-alkoxy hydroperoxide, trapping of the generated alkyl radical with 2,2,6,6-tetramethylpiperidin-1-yl (TEMPO), and subsequent oxidative fragmentation with MMPP. Using readily available starting materials from chiral pool, a variety of carbonyl-containing products have been accessed rapidly in good yields.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
Alkynes to Carboxylic Acids: Oxidative Cleavage
Oxidative Cleavage of Alkenes: Ozonolysis
Ozone is a symmetrical bent molecule stabilized by a resonance structure.
Radical Anti-Markovnikov Addition to Alkenes: Overview
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Ethers to Alkyl Halides: Acidic Cleavage
C–C Bond Cleavage: Retro-Aldol Reaction
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.