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Related Concept Videos

Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

11.8K
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...
11.8K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.6K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
14.6K
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

10.6K
Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The...
10.6K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.2K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.2K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

12.5K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
12.5K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

18.3K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
18.3K

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Updated: Jun 28, 2025

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Angle-strained sila-cycloalkynes.

Herbert Wakefield1, Sophia J Melvin1, Jennifer Jiang1

  • 1Department of Chemistry, Johns Hopkins University, 3400 N. Charles St, Baltimore, MD 21218, USA. Klausen@jhu.edu.

Chemical Communications (Cambridge, England)
|April 15, 2024
PubMed
Summary
This summary is machine-generated.

Novel silicon-containing cycloalkynes were synthesized and found to be angle-strained. These strained sila-cyclooctynes showed low reactivity in cycloaddition reactions, indicating strain

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Area of Science:

  • Organosilicon chemistry
  • Cycloalkyne synthesis
  • Strain engineering

Background:

  • Second-row elements influence ring strain in small- and medium-sized rings.
  • Understanding strain modulation is key for designing reactive molecules.

Purpose of the Study:

  • To synthesize novel oligosilyl-containing cycloalkynes.
  • To investigate the impact of silicon incorporation on ring strain.
  • To evaluate the reactivity of these strained cycloalkynes in cycloaddition reactions.

Main Methods:

  • Synthesis of novel sila-cyclooctynes.
  • X-ray crystallography for structural analysis.
  • Density functional theory (DFT) calculations for distortion-interaction model analysis.

Main Results:

  • Two novel oligosilyl-containing cycloalkynes were successfully synthesized.
  • X-ray crystallography confirmed significant angle-strain in the sila-cyclooctynes.
  • The angle-strained sila-cyclooctynes exhibited sluggish reactivity in cycloadditions with benzyl azide.

Conclusions:

  • Incorporation of second-row elements like silicon can introduce significant angle-strain in cycloalkyne rings.
  • Despite inherent strain, these sila-cyclooctynes display reduced participation in cycloaddition reactions.
  • Strain-interaction model analysis provides insights into the reactivity of strained silicon-containing rings.