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Related Concept Videos

Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

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,...
Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

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Related Experiment Video

Updated: May 16, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Phthalocrowns: isoindoline-crown ether macrocycles.

Ingrid-Suzy Tamgho1, James T Engle, Christopher J Ziegler

  • 1Department of Chemistry, University of Akron, Akron, Ohio 44325-3601, USA.

The Journal of Organic Chemistry
|November 29, 2012
PubMed
Summary
This summary is machine-generated.

Diiminoisoindoline reacts with polyethers to form phthalocrown macrocycles. The number of ether units dictates reaction type and stability, with n=1 showing dynamic proton exchange.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Macrocyclic Chemistry

Background:

  • Diiminoisoindoline serves as a precursor for macrocycle synthesis.
  • Amine-terminated polyethers are utilized as building blocks for crown ether derivatives.
  • Understanding macrocycle formation and stability is crucial in supramolecular chemistry.

Purpose of the Study:

  • To investigate the synthesis of phthalocrown macrocycles via the reaction of diiminoisoindoline with amine-terminated polyethers.
  • To determine the influence of polyether chain length (number of ether units, n) on macrocycle formation and stability.
  • To characterize the dynamic behavior and proton exchange kinetics in the synthesized phthalocrowns.

Main Methods:

  • Condensation reaction between diiminoisoindoline and amine-terminated polyethers with varying numbers of ether units (n=1, 2, 3).
  • Spectroscopic analysis, including proton Nuclear Magnetic Resonance ((1)H NMR), to confirm macrocycle formation and structure.
  • Variable Temperature Nuclear Magnetic Resonance (VTNMR) spectroscopy to study dynamic processes and determine activation energy for proton exchange.

Main Results:

  • Phthalocrown macrocycles were successfully synthesized.
  • A 2+2 condensation occurred for n=1, while 1+1 macrocycle formation was observed for n=2 and n=3.
  • The n=2 phthalocrown exhibited high stability attributed to intramolecular hydrogen bonding.
  • The n=3 phthalocrown underwent hydrolysis, yielding a derivatized crown ether species.
  • Dynamic behavior and proton exchange were observed for the n=1 phthalocrown, with a measured activation energy (ΔG‡) of 44.6 kJ/mol.

Conclusions:

  • The synthetic strategy allows for controlled formation of phthalocrown macrocycles.
  • Macrocycle structure, stability, and reactivity are dependent on the polyether chain length.
  • The n=1 phthalocrown displays interesting dynamic properties indicative of proton exchange mechanisms.