electrons dance around a cyclic transition state during electrocyclisation

Categories: Comparisons, Idioms

An example of the use of metaphor (and an English idiom) in science journalism:

"Long-time readers of this column will know that I love a cycloaddition – I've probably run hundreds of them over my career as an organic chemist. There was even a two-hour period immediately before my PhD viva where I could credibly claim to understand the fiendishly complex Woodward-Hoffman rules that were used to rationalise their outcomes in the pencil-and-paper days before computational chemistry. However, I have far less experience with their rarer cousin, the electrocyclisation.
On the surface, these reactions are pretty simple: electrons dance around a cyclic transition state, resulting in a double bond lost and a single bond gained.

A great example of a recent total synthesis that hinges on a couple of well-chosen (but well-hidden) electrocyclisations is the route taken to the phomopsene diterpenes by Yong-Qiang Tu of Shanghai Jiao Tong University and Lanzhou University, China, and co-workers.

The route more-or-less begins with a Nazarov cyclisation/ring expansion cascade, an unbelievable disconnection that's about as obvious as a black cat in a coal cellar. "

Chris Nawra (2013) (+)-iso-Phomopsene (and friends), Chemistry World, October 2023, p.13. https://www.chemistryworld.com/opinion/-iso-phomopsene-and-friends/4018109.article

Author: Keith

Former school and college science teacher, teacher educator, research supervisor, and research methods lecturer. Emeritus Professor of Science Education at the University of Cambridge.