Electrocatalytic Epoxidation of Cyclooctene

  • Author: ChemistryViews.org
  • Published: 11 April 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Electrocatalytic Epoxidation of Cyclooctene

Epoxides are useful intermediates in synthetic organic chemistry. Existing methods for the epoxidation of allenes usually require harsh, hard-to-handle oxidants and/or produce stoichiometric amounts of byproducts.


Karthish Manthiram and colleagues, Massachusetts Institute of Technology (MIT), Cambridge, USA, have developed a sustainable, simple-to-operate electrocatalytic epoxidation protocol. The reaction uses manganese oxide nanoparticles as the catalyst and water as the source for oxygen atoms. Manganese oxide nanoparticles were drop-cast onto a hydrophilic carbon paper and then annealed at 400 °C. The resulting material was used as the working electrode, platinum foil was used as counterelectrode, and acetonitrile with added tetrabutylammonium tetrafluoroborate was used as the solvent for the electrochemical reaction of cis-cyclooctene and water. The reaction was performed at ambient conditions.


The desired cyclooctene oxide (pictured) was obtained with over 30 % Faradaic efficiency and with molecular hydrogen as the only stoichiometric byproduct. Control experiments with H218O confirmed that water acts as the oxygen source. According to the researchers, the developed approach could represent a new way to catalyze oxygen atom transfer reactions electrochemically.


 

Article Views: 466

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH