At a Glance
- UCLA chemists have challenged Bredt’s rule, a long-standing concept in organic chemistry that restricts specific molecular structures with double bonds.
- Bredt’s rule, established in 1924, stated that double bonds could not exist at the “bridgehead” of bicyclic molecules without distorting their structure, limiting the development of certain molecular forms.
- The research team, led by Professor Neil Garg, synthesized anti-Bredt olefins (ABOs), a new class of molecules that defy Bredt’s rule, using fluoride compounds to stabilize these typically unstable structures.
- This breakthrough opens up potential applications in drug discovery and pharmaceutical research, as ABOs can be used to create complex, valuable compounds.
- The findings may lead to a significant shift in organic chemistry, allowing for the development of novel molecules and rewriting established knowledge in the field.
Chemists at UCLA have recently overturned a long-standing rule in organic chemistry that has been taught for nearly a century. The rule, known as Bredt’s rule, suggested that certain molecules could not have double bonds at specific positions, a concept fundamental to the study of organic chemistry. However, in a breakthrough study published in Science, the team showed that it is possible to create molecules that defy Bredt’s rule, allowing for the synthesis of new kinds of molecules with exciting potential applications.
The UCLA team focused on molecules called olefins, which contain a double bond between two carbon atoms. These molecules usually have a specific, rigid shape. Bredt’s rule, formulated in 1924, stated that a double bond at the “bridgehead” position in a bicyclic molecule could not exist without distorting the molecule’s structure. This rule limited chemists’ ability to explore specific types of chemical structures and hindered the development of new molecules, especially for pharmaceutical research.
However, the UCLA researchers, led by Professor Neil Garg, demonstrated a way to break this rule. They synthesized a new type of molecule, called anti-Bredt olefins (ABOs), which are unstable but can be created and “trapped” to study. By using a chemical process that included fluoride compounds to induce the creation of these molecules, the researchers successfully generated ABOs, showing they could be used to create valuable compounds with complex structures. These findings challenge what was once considered impossible in organic chemistry.
The discovery could open up new possibilities in drug discovery and other areas of chemistry, as ABOs can now be used to develop novel molecules for practical use. Professor Garg and his team are excited by the potential to rewrite textbooks on organic chemistry and explore how these newly discovered molecules can be used to create valuable compounds. The ability to manipulate these molecules could revolutionize areas like pharmaceutical development, making it easier to create new drugs and other valuable chemicals.
References
- McDermott, L., Walters, Z. G., French, S. A., Clark, A. M., Ding, J., Kelleghan, A. V., Houk, K. N., & Garg, N. K. (2024). A solution to the anti-Bredt olefin synthesis problem. Science, 386(6721), eadq3519. https://doi.org/10.1126/science.adq3519
- University of California Los Angeles. (2024, October 31). Chemists just broke a 100-year-old rule and say it’s time to rewrite the textbooks. Phys.Org; University of California Los Angeles. https://phys.org/news/2024-10-chemists-broke-year-rewrite-textbooks.html
