The Bredt’s Rule

Bredt’s rule, established by German chemist Carl Bredt in 1909, states that all alkenes with three or more double bonds must have at least one methyl group attached to the double bond. This rule has been a cornerstone of organic chemistry for over a century, guiding chemists in the synthesis and analysis of alkenes. However, the discovery of the new molecule has challenged this long-held principle.

The Discovery

Researchers at the University of California, Los Angeles (UCLA) have identified a molecule that defies Bredt’s rule. This molecule, which has not been named yet, contains three double bonds and no methyl group attached to any of the double bonds. The team, led by Dr.

Double bonds: a theoretical puzzle that sparked intense debate among chemists.

The Double Bond Conundrum

The concept of a double bond in organic chemistry has long been a topic of debate. Julius Bredt, a renowned chemist, proposed that a double bond was impossible in his 1924 paper. This assertion sparked intense discussion and experimentation among chemists, with some attempting to prove or disprove his claim.

Theoretical Background

To understand the double bond conundrum, it’s essential to delve into the theoretical background.

This is a common feature of norbornene and its derivatives.

Introduction

Norbornene is a type of unsaturated hydrocarbon that has gained significant attention in the field of organic chemistry. Its unique structure, which features a seven-membered ring with a double bond, makes it an attractive molecule for various applications. In this article, we will delve into the properties and uses of norbornene, exploring its chemical behavior, synthesis, and potential applications.

Chemical Structure and Properties

Norbornene’s molecular structure consists of a seven-membered ring with a double bond, which gives it a distinctive peak in its NMR spectrum.

Theoretical Approach

The team of UCLA chemist Neil Garg began their research by exploring the theoretical aspects of bicyclic rings with an anti-Bredt bond. They used computational models to simulate the behavior of these compounds, which allowed them to predict the most stable arrangements of the rings.

This combination allowed for the creation of a wide range of compounds with unique properties.

Understanding the Importance of Three-Dimensional Structures in Medicinal Chemistry

The quest for new medicines has led chemists to develop innovative methods for creating three-dimensional structures that can be used to discover new treatments. One such approach involves combining silyl (pseudo)halide precursors with another fluoride-containing molecule. This strategy has proven to be highly effective in generating a diverse array of compounds with distinct properties.

The Role of Silyl (Pseudo)Halide Precursors

Silyl (pseudo)halide precursors play a crucial role in the creation of these three-dimensional structures. These precursors are highly reactive and can be easily modified to form a wide range of compounds.

“What this study shows is that contrary to one hundred years of conventional wisdom, chemists can make and use anti-Bredt olefins to make value-added products.”