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Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

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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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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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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Ring expansion of a ring expanded carbene.

Lucía García1, Khalidah H M Al Furaiji2, David J D Wilson2

  • 1Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK. m.s.hill@bath.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|August 30, 2017
PubMed
Summary

Phenylsilane reacts with a ring-expanded carbene, forming a diorganosilane via Si-H addition. Subsequent heating triggers ring expansion through silicon-carbon bond migration.

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Area of Science:

  • Organosilicon Chemistry
  • Carbene Chemistry

Background:

  • Carbenes are reactive intermediates with diverse applications.
  • Organosilanes are versatile compounds in synthetic chemistry.

Purpose of the Study:

  • To investigate the reaction between phenylsilane and a specific ring-expanded carbene.
  • To explore the mechanism of Si-H oxidative addition and subsequent ring expansion.

Main Methods:

  • Room temperature reaction of phenylsilane with 6-Mes carbene.
  • Thermal treatment of the resulting diorganosilane.

Main Results:

  • Facile Si-H oxidative addition to the carbenic carbon was observed at room temperature.
  • Ring expansion occurred upon heating, involving migration of Si-H or Si-Ph bonds.

Conclusions:

  • The study demonstrates a novel pathway for carbene functionalization with organosilanes.
  • The findings offer insights into silicon-carbon bond activation and ring expansion mechanisms.