UCLA researchers have invalidated Bredt’s rule, a fundamental principle of organic chemistry that has constrained molecular design for 100 years.
Why it matters: This breakthrough opens new possibilities for drug discovery and pharmaceutical development. The finding challenges long-held assumptions about what molecular structures are possible in organic chemistry.
- Bredt’s rule, established in 1924, claimed certain carbon-carbon double bond arrangements were impossible in bridged bicyclic molecules.
Key finding: The team successfully created and trapped anti-Bredt olefins (ABOs), proving these supposedly “impossible” molecular structures can exist and be useful.
“We shouldn’t have rules like this—or if we have them, they should only exist with the constant reminder that they’re guidelines, not rules.”
Neil Garg, UCLA’s Kenneth N. Trueblood Distinguished Professor of Chemistry
The process:
- Researchers treated silyl (pseudo)halides with fluoride
- Used chemical traps to capture unstable ABO molecules
- Demonstrated practical value through isolation of resulting products
Keep in mind: While these molecules are highly unstable, the team’s method for trapping them makes them practically useful for the first time.
Real-world impact: This discovery could revolutionize pharmaceutical research by:
- Enabling the creation of new 3D molecular structures
- Expanding the toolkit for drug discovery
- Challenging other “unchangeable” rules in chemistry
TL;DR
- A 100-year-old chemistry rule about molecular structures has been disproven by UCLA researchers.
- The breakthrough enables the creation of previously “impossible” molecular structures.
- This discovery could accelerate drug development and pharmaceutical research.
Read the Paper
A solution to the anti-Bredt olefin synthesis problem