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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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...
2.9K
Cycloalkanes02:28

Cycloalkanes

12.9K
Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...
12.9K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

11.9K
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...
11.9K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.7K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.9K
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...
14.9K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

12.8K
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...
12.8K

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Updated: Aug 19, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
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Carbene Routes to Cyclopropatetrahedrane.

Murray G Rosenberg1, Udo H Brinker2,1

  • 1Department of Chemistry, The State University of New York at Binghamton, P.O. Box 6000, Binghamton, New York 13902-6000, United States.

The Journal of Organic Chemistry
|November 29, 2022
PubMed
Summary
This summary is machine-generated.

Computational chemistry explored the synthesis of cyclopropatetrahedrane (tetracyclo[2.1.0.01,3.02,4]pentane) through four carbene reactions. Results confirm direct cyclopropanation pathways and analyze transition state energies for each step.

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Area of Science:

  • Computational chemistry
  • Quantum chemistry
  • Organic synthesis

Background:

  • Cyclopropatetrahedrane is a strained polycyclic hydrocarbon.
  • Carbene reactions are fundamental in organic synthesis.

Purpose of the Study:

  • To computationally investigate the formation of cyclopropatetrahedrane via carbene reactions.
  • To elucidate the reaction mechanisms and transition states involved.

Main Methods:

  • Utilizing the (U)CCSD(T)(full)/cc-pVTZ//(U)ωB97X-D/cc-pVTZ + 1.3686(EZPVE) theoretical model.
  • Employing intrinsic reaction coordinate (IRC) plots to analyze reaction pathways.
  • Assessing the structure and energy of transition states for each elementary step.

Main Results:

  • Four distinct carbene reactions were computed, all leading to cyclopropatetrahedrane.
  • Intrinsic reaction coordinate plots confirmed direct cyclopropanation steps for each carbene.
  • Transition state analysis provided insights into the energetics and structural features of the reaction pathways.

Conclusions:

  • The study confirms the feasibility of synthesizing cyclopropatetrahedrane through specific carbene reactions.
  • The computational model successfully characterized the reaction mechanisms and transition states.
  • This research provides a theoretical foundation for experimental investigations into cyclopropatetrahedrane synthesis.