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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

14.0K
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...
14.0K
Constitutional Isomers of Alkanes02:18

Constitutional Isomers of Alkanes

21.7K
Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the...
21.7K
Nomenclature of Alkanes02:22

Nomenclature of Alkanes

25.9K
In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature.
The alkane nomenclature considers the length of the carbon chain, the number, and the location of the substituent to arrive at its systematic name. The IUPAC...
25.9K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.5K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.5K
Nomenclature of Alkenes02:29

Nomenclature of Alkenes

14.9K
The IUPAC naming system for alkenes replaces -an- with -en- in the corresponding parent alkanes. Accordingly, a simple alkene replaces the -ane suffix of the alkane with -ene.
As per the IUPAC rules, the longest carbon chain containing the maximum number of double bonds is identified as the parent chain and is numbered such that the doubly bonded carbon atoms receive the lowest possible numbers. The location of the double bond is indicated by the number of its first carbon atom. In branched...
14.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.6K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.6K

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Updated: Jan 14, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Propellane-free access to bicyclo[1.1.1]pentanes.

Chang Liu1, Wenyuan Li1, Renzhe Li1

  • 1Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, TX, USA.

Nature Communications
|January 12, 2026
PubMed
Summary
This summary is machine-generated.

Bicyclo[1.1.1]pentane (BCP) is a key 3D molecule in drug discovery. New propellane-free methods enable synthesis of complex BCPs, advancing medicinal chemistry.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Drug Discovery

Background:

  • Bicyclo[1.1.1]pentane (BCP) is a 3D bioisostere for benzene, enhancing drug properties.
  • Traditional synthesis relies on [1.1.1]propellane, limiting access to complex BCP derivatives.

Purpose of the Study:

  • To review recent propellane-free synthetic strategies for multisubstituted and bridge-functionalized BCPs.
  • To assess the scope and limitations of emerging BCP synthesis methodologies.

Main Methods:

  • Intramolecular diradical couplings
  • Carbene-mediated ring expansions
  • Two-electron disconnections

Main Results:

  • Emerging methods offer alternatives to propellane-based BCP synthesis.
  • These strategies facilitate access to highly strained and sterically hindered BCPs.
  • The reviewed methods expand the toolkit for medicinal chemists.

Conclusions:

  • Propellane-free routes are crucial for accessing diverse BCP scaffolds.
  • Further synthetic development is needed to address remaining challenges.
  • Advanced BCP derivatives hold significant potential for pharmaceutical research.