A team of scientists led by Professor Neil Garg is redefining a fundamental principle in organic chemistry. Bredt’s rule, which has been a cornerstone of the field since 1924, may not be as unbreakable as thought.
Bredt’s rule states that double bonds cannot exist at certain positions within bridged bicyclic molecules, known as olefins. However, Garg and his colleagues have found a way to create these molecules, called anti-Bredt olefins (ABOs), which defy this long-standing rule.
To achieve this breakthrough, the researchers used a clever approach involving silyl (pseudo)halides treated with fluoride sources. They then employed another chemical to “trap” these unstable molecules, allowing them to capture and study ABOs.
This discovery opens up new possibilities for drug discovery, as ABOs can be used to create three-dimensional structures that have potential applications in medicine. By challenging Bredt’s rule, Garg’s team is advocating for a more flexible and innovative approach to chemistry.
The findings highlight the importance of questioning assumptions and pushing boundaries in scientific research. If a century-old rule can be broken, it underscores the potential for future breakthroughs. As Garg noted, “chemists can make and use anti-Bredt olefins to make value-added products.” This discovery is a stepping stone to numerous possibilities in organic chemistry, pharmaceuticals, and other fields of study.
Source: https://www.earth.com/news/100-year-old-chemistry-rule-bredts-rule-proven-false-updating-textbooks-comes-next