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Related Concept Videos

Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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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...
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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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...
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.6K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

13.9K
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...
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Conformations of Ethane and Propane02:18

Conformations of Ethane and Propane

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In an organic molecule, free rotation about the carbon-carbon single bond results in energetically different conformers of the molecule. Due to this rotation, called the internal rotation, ethane has two major conformations — staggered and eclipsed.
Staggered conformation is a low energy and more stable conformation with the C-H bonds on the front carbon placed at 60°dihedral angles relative to the C-H bonds on the back carbon, leading to a reduced torsional strain. In staggered...
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Conformational Design Principles in Total Synthesis.

Renzhi Chen1, Yang Shen1, Sihan Yang1

  • 1Department of Chemistry and Key Laboratory of Chemical Biology of Fujian Province, iChEM, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, 361005, China.

Angewandte Chemie (International Ed. in English)
|April 15, 2020
PubMed
Summary
This summary is machine-generated.

Conformational design is crucial in organic chemistry for controlling molecular shape and influencing properties. This review highlights its impact on synthesizing complex natural products over the past 20 years.

Keywords:
C−H functionalizationconformational designring formationstereochemistrytotal synthesis

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Synthetic Chemistry

Background:

  • Conformation is fundamental for understanding molecules in 3D.
  • Molecular conformation impacts physical, chemical, and biological properties.
  • Conformational design is key in synthesizing complex natural products.

Purpose of the Study:

  • To review conformational design in natural product synthesis.
  • To emphasize applications and insights from the last 20 years.
  • To categorize examples by substrate structural features.

Main Methods:

  • Highlighting selected examples of conformational design.
  • Focusing on applications in natural product synthesis.
  • Categorizing examples into open-chain, cyclohexane, and ring types.

Main Results:

  • Conformational design plays a critical role in synthesis.
  • It guides bond formation, stereocenter creation, and ring construction.
  • Recent advances have provided new insights into its application.

Conclusions:

  • Conformational design is a powerful strategy in organic synthesis.
  • Its application is vital for the efficient synthesis of complex molecules.
  • Understanding and controlling conformation enables precise molecular construction.