Chemistry 2011.org
Chemistry2011.org
All About Chemistry... 2011 and beyond
Synthesis, Compounds

Related Stories

Chemical synthesis: A simple technique for highly functionalized compounds

Sep. 25, 2013 — Researchers at Kanazawa University have demonstrated a technique that allows direct functionalization of alkenes without the need for metallic reagents, photolysis or extreme reaction conditions.

The addition of functional groups to certain unsaturated hydrocarbons, known as alkenes, is a crucial stage in the synthesis of various compounds, including many plastics.

For these functionalization reactions to occur a carbon-hydrogen (C-H) bond must be activated, which is traditionally achieved using transition metal catalysts. However use of these catalysts has both economical and environmental drawbacks. Now researchers at Kanazawa University have demonstrated a technique that allows direct functionalization of alkenes without the need for metallic reagents, photolysis or extreme reaction conditions.

Tsuyoshi Taniguchi and colleagues at Kanazawa University developed work where they had reported a reaction of alkenes using tert-butyl nitrite and molecular oxygen. They monitored the reaction products -- ɣ-lactol and nitrate ester -- using different solvents, and found that a high polarity aprotic (hydrogen-free) solvent gave the best yield, with ɣ-lactol as the major product.

They then experimented with different alkenes and observed how the products differed for branched and linear alkenes. Further reduction reactions demonstrated how the new synthesis technique could yield a range of useful derivatives, producing highly functionalized compounds from simple alkenes in only one or two steps.

The researchers were also able to propose a possible reaction mechanism. While the exact pathway remains uncertain, they suggest that the key step is the cleavage of an oxygen-oxygen bond to form a highly reactive alkoxy radical -- a molecular component comprising an oxygen with single bonds either side to hydrocarbon chains.

The work demonstrates how substantial yields of highly functionalized compounds can be achieved from simple organic molecules in simple conditions with no metal catalyst. The authors conclude, "We believe that such 'simple and advanced reactions' are promising in the development of useful synthetic methods involving direct C-H functionalization."

Share this story with your friends!

Social Networking

Please recommend us on Facebook, Twitter and more:

Other social media tools

Global Partners
Feedback

Tell us what you think of Chemistry 2011 -- we welcome both positive and negative comments. Have any problems using the site? Questions?

About us

Chemistry2011 is an informational resource for students, educators and the self-taught in the field of chemistry. We offer resources such as course materials, chemistry department listings, activities, events, projects and more along with current news releases.

Events & Activities

Are you interested in listing an event or sharing an activity or idea? Perhaps you are coordinating an event and are in need of additional resources? Within our site you will find a variety of activities and projects your peers have previously submitted or which have been freely shared through creative commons licenses. Here are some highlights: Featured Idea 1, Featured Idea 2.

About you

Ready to get involved? The first step is to sign up by following the link: Join Here. Also don’t forget to fill out your profile including any professional designations.

Global Partners