Turbo-charged Diels-Alder reaction


diels-alder

This new Diels-Alder forms an aryne from an alkyne and diyne © NPG

The Diels–Alder reaction is one that sticks in the mind of even the most reluctant chemistry student – there is a certain elegance in the ring formation from an alkene and diene. Analogous reactions, with further oxidised reactants, have been reported previously, forming a cyclo-hexadiene (in the didehydro-Diels-Alder) or benzene (tetradehydro-Diels-Alder). This latest discovery takes this even further to react an alkyne and diyne in the hexadehydro-Diels-Alder to form an aryne.

Arynes are widely-used reactive intermediates and this new method of generating them could expand their usage even further. The aryne intermediates formed could be used to react with other reagents or react intramolecularly.

The authors of the paper, from the University of Minnesota, USA, expressed their surprise that this method had not been exploited previously. Indeed, they only came across the reaction by chance in the course of a separate synthesis.


Related Content

Mandelalide A

8 May 2014 Organic Matter

news image

New reactions need to belong in a synthesis, says BRSM, not be forced in for show

Kingianin A

1 May 2013 Totally Synthetic

news image

Paul Docherty faces his fears of frontier molecular orbital theory

Most Read

Sun rises on new solar route to hydrogen

27 February 2015 Research

news image

Photocatalyst has solar-to-hydrogen conversion efficiency of 2% and points way to cheap production of the gas

Chemists zinc up ‘aromatic’ metal cubes

2 March 2015 Research

news image

Metal-organic clusters share electrons between eight covalently linked metal atoms

Most Commented

Sun rises on new solar route to hydrogen

27 February 2015 Research

news image

Photocatalyst has solar-to-hydrogen conversion efficiency of 2% and points way to cheap production of the gas

Hepatitis C drug patent challenged in Europe

19 February 2015 Business

news image

Campaign group says Gilead’s expensive blockbuster sofosbuvir is not innovative enough to warrant a patent