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Structure and Nomenclature of Epoxides02:38

Structure and Nomenclature of Epoxides

Cyclic ethers are heterocyclic compounds with an oxygen atom in the ring along with carbon atoms. They are named depending on the number of carbon atoms present in their ring system. Cyclic ethers with a three-membered ring system are called “oxirane”, four-membered ring systems as “oxetane”, five-membered ring systems as “oxolane”, and six-membered ring systems as “oxane”. The cyclic structure of these rings imposes angle strain, and this strain is more in the ring having a smaller number of...
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Nomenclature of Aryl and Heterocyclic Amines

The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
Classification of Ethers
Based on their attached substituent groups, ethers can be classified into two...
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Poly(cyclic imino ether)s beyond 2-substituted-2-oxazolines.

Meta M Bloksma1, Ulrich S Schubert, Richard Hoogenboom

  • 1Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology, The Netherlands.

Macromolecular Rapid Communications
|June 30, 2011
PubMed
Summary

This study explores alternative cyclic imino ether monomers, including 2-oxazines and chiral 2-oxazolines, for cationic ring-opening polymerization (CROP). It highlights their potential to expand polymer versatility and discusses polymer properties and hydrolysis.

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Area of Science:

  • Polymer Chemistry
  • Organic Chemistry

Background:

  • 2-Oxazolines (2-OZO) are well-studied cyclic imino ethers for cationic ring-opening polymerization (CROP).
  • Alternative cyclic imino ethers, such as 6- and 7-membered rings and chiral 4- and 5-substituted 2-OZO, offer expanded possibilities.

Purpose of the Study:

  • To review the polymerization of 2-oxazines (2-OZI) and chiral 4- and 5-substituted 2-OZO via CROP.
  • To discuss the properties of the resulting polymers.
  • To address the hydrolysis of these polymers into poly(alkylene imine)s.

Main Methods:

  • Overview of cationic ring-opening polymerization (CROP) mechanisms for various cyclic imino ethers.
  • Characterization of polymer properties derived from alternative monomers.
  • Investigation of polymer hydrolysis pathways.

Main Results:

  • Demonstration of successful CROP for 2-oxazines and chiral 2-oxazolines.
  • Characterization of unique polymer properties achievable with these monomers.
  • Understanding of the hydrolysis behavior of novel poly(cyclic imino ether)s.

Conclusions:

  • Alternative cyclic imino ethers like 2-oxazines and chiral 2-oxazolines significantly enhance the versatility of (co)poly(cyclic imino ether)s.
  • These monomers offer new avenues for designing polymers with tailored properties.
  • Hydrolysis provides a route to poly(alkylene imine)s from these novel polymer structures.