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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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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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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.
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Conformations of Cycloalkanes02:29

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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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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.
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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.
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Terpenoid Cyclophanes with Planar Chirality.

Alina Trofimova1, Matthew Diamandas1, Chelsey Brien1

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto M5S 3H6, Canada.

Journal of the American Chemical Society
|August 12, 2024
PubMed
Summary
This summary is machine-generated.

Chiral cyclophanes synthesized from natural terpenes like citronellol exhibit significant ring strain. This strain influences their stability and reactivity, leading to unexpected isomer formation.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Stereochemistry

Background:

  • Cyclophanes are cyclic organic compounds known for their unique structural properties.
  • Strain-induced chirality in cyclophanes is an area of active research interest.
  • Terpenes are natural products with diverse applications in synthesis.

Purpose of the Study:

  • To synthesize novel anilinocyclophanes using naturally occurring terpenes.
  • To investigate the impact of ring strain on the chirality and properties of these cyclophanes.
  • To explore the reactivity and stability influenced by strain in terpenoid para-cyclophanes.

Main Methods:

  • Synthesis of anilinocyclophanes from citronellol, geraniol, and farnesol.
  • Characterization of cyclic oligoprenyl molecules.
  • Analysis of ring strain using computational or experimental methods (implied).
  • Investigation of chirality across aryl rings and double bonds.

Main Results:

  • Successful synthesis of anilinocyclophanes derived from natural terpenes.
  • Demonstration of considerable ring strain (up to 31 kcal/mol) in the synthesized molecules.
  • Observation of chirality associated with the aryl ring and double bonds.
  • Formation of unexpected isomers, such as isomerized neraniline.

Conclusions:

  • The synthesized terpenoid para-cyclophanes exhibit significant ring strain and chirality.
  • Ring strain plays a crucial role in the stability and reactivity of these molecules.
  • The study provides insights into the synthesis and behavior of strained cyclic systems derived from natural products.