A team of chemists from the University of California, Los Angeles (UCLA) has upended a century-old rule in organic chemistry known as Bredt’s Rule. This rule, first established by German chemist Julius Bredt in 1924, states that stable double bonds can’t form next to certain bridge structures within “bicyclic” molecules structures often compared to figure eights. Bredt’s Rule has long held chemists back from experimenting with such double bonds due to assumed instability, making certain molecular structures seemingly impossible to create.
But UCLA chemist Neil Garg and his team have shown that anti-Bredt olefins double bonds positioned adjacent to bridgeheads are indeed achievable. Garg argues that such rules, while useful, can limit creative exploration in chemistry. “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. It destroys creativity when we have rules that supposedly can’t be overcome,” says Garg.
By using a theoretical approach and a strategic method developed by organic chemist Shu Kobayashi, the UCLA team managed to synthesize anti-Bredt olefins successfully. This process involved combining special precursors with fluoride-containing molecules and other chemicals to stabilize the double bond.
Breaking Bredt’s Rule opens up new avenues for synthetic compounds that could revolutionize drug discovery. In pharmaceutical development, the search for complex three-dimensional structures is crucial for creating innovative medicines. Garg believes this discovery could lead to “value-added products” that were previously off-limits due to Bredt’s Rule, providing new opportunities for the industry.
This breakthrough demonstrates that even “impossible” structures can be within reach, paving the way for chemists to explore new reactions and design molecules with untapped medicinal potential.
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