Chemists Create ‘Impossible’ Bond in Molecule, Defying 100-Year-Old Rule

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A team of chemists from the University of California, Los Angeles has made a groundbreaking discovery that breaks a century-old rule established by Bredt. This breakthrough will likely pave the way for drug researchers to investigate molecules previously thought impossible.

They seem to disprove his theory.

As any amateur furniture assembler is aware, geometry plays a crucial role in ensuring that your self-assembled bookshelf doesn’t collapse into a pile of splinters.

Organic chemistry isn’t all that dissimilar – while some joins can allow for some flexibility and adjustment, others unyielding demand the existing structure remain perfectly straight before coming into place.

It might resemble the figure eight on a digital clock display.

It’s possible to add a carbon atom to the center of the molecule, causing it to intersect with the middle bond, resulting in a peak referred to as a bridgehead. At the same time, the rest of the molecule adjusts its positioning, preventing the figure-eight shape from lying flat on its side.

Do you want to add a second bond to one of the carbons on either end of your bridgehead to create an organic compound known as an alkene?

Unfortunately, it’s your bad luck.

University of California Los Angeles chemist Neil Garg is against the Bredt rule. He recommends giving it a try.

Garg.

We shouldn’t have regulations like this – or if we do, they should only be suggestions, with a constant reminder that they’re not set in stone. It stifles creativity when we have rules that supposedly can’t be broken.

To plan a suitable set of precursor compounds and routes that will encourage the formation of a double bond.

The successful plan incorporated silyl (pseudo)halide precursors with another fluoride compound along with a set of stabilizing chemicals that enabled the bond to be formed and the product to be separated.

It’s a challenge to make new methods to create compounds that were previously considered unattainable, adding to the variety of synthetic compounds that could have practical uses.

Garg.

This study shows that going against a century of conventional thinking, chemists can create and apply anti-Bredt olefins to produce more valuable compounds.

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