Do Anti-Bredt Natural Products Exist? Olefin Strain Energy as a Predictor of Isolability

Elizabeth H Krenske1, Craig M Williams2

  • 1School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland (Australia) http://www.scmb.uq.edu.au/homepages/williams/index.html. e.krenske@uq.edu.au.

Related Concept Videos

Relative Stabilities of Alkenes01:59

Relative Stabilities of Alkenes

The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene.  The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
16.2K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
16.8K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
4.7K
Strain and Elastic Modulus01:15

Strain and Elastic Modulus

The quantity that describes the deformation of a body under stress is known as strain. Strain is given as a fractional change in either length, volume, or geometry under tensile, volume (also known as bulk), or shear stress, respectively, and is a dimensionless quantity. The strain experienced by a body under tensile or compressive stress is called tensile or compressive strain, respectively. In contrast, the strain experienced under bulk stress and shear stress is known as volume and shear...
9.3K
Biofuels01:25

Biofuels

The microbial conversion of organic matter into biofuels holds potential as a renewable energy source. Among biofuel sources, microalgae are recognized as a highly efficient and adaptable feedstock for biodiesel production, owing to their rapid biomass accumulation, elevated lipid productivity, and capacity to proliferate in diverse aquatic systems, including freshwater, marine, and wastewater habitats. Unlike terrestrial crops, microalgae do not compete for land and can achieve significantly...
78
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
2.8K