Ring-Forming Polymerizations Pt B 1 - 1st Edition - ISBN: 9780121917029, 9780323150019

Ring-Forming Polymerizations Pt B 1

1st Edition

Heterocyclic Rings

Authors: Robert Cotter
eBook ISBN: 9780323150019
Imprint: Academic Press
Published Date: 1st January 1972
Page Count: 446
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Ring-Forming Polymerizations, Part B, 1: Heterocyclic Rings presents a comprehensive review and compilation of ring-forming polymerization reactions that proceed with the formation of heterocyclic rings. Emphasis is placed on polymerizations leading to linear, high molecular weight products. This book is comprised of three chapters and begins with a discussion on polymerizations that result in the formation of a multiple bond containing at least one heteroatom. The condensation of amines with carbonyl compounds to yield poly(Schiff bases) and related polymers is examined, along with other carbon-nitrogen double bond-forming polymerizations. The next chapter is devoted to the polymerization of rings containing two carbon atoms, including the polymerization of polyphenols with diboronic acids and that of diisocyanides with triorganoborons. The last chapter describes the polymerization of rings containing three carbon atoms, with particular reference to polyisoxazoles and related polymers, polythiazoles, polyimidazoles and related polymers, polypyrazoles, and polytriazines. This monograph will be of interest to polymer and organic chemists and others who are concerned with the polymer chemistry of living systems.

Table of Contents


Contents of Part A

Contents of Part B


Chapter I. Multiple Bond-Forming Polymerizations

A. Poly(Schiff Bases) and Related Polymers

Method 1. Polymerization of Dicarbonyl Compounds with Diamines

Method 2. Bulk Polymerization of Dicarbonyl Compounds with Diamines

Method 3. Polymerization of Cyclic Oligomeric Schiff Bases Properties of Poly(Schiff Bases)

B. Other Carbon-Nitrogen Double Bond-Forming Polymerizations

Method 1. Polymerization of Monomers Containing Nitrile Groups

Method 2. Dehydrative Polymerization of Nitrile Precursor Monomers

Method 3. Polyrecombination of Nitriles

Method 4. Polymerization of Isonitriles

C. Poly Carbodiimides

Method 1. Polymerization of Diisocyanates

Method 2. Polymerization by Exchange with Monomeric Carbodiimides

Method 3. Pyrolysis of Bis(Urethans)

Method 4. Oxidative Desulfurization of Poly(Thioureas)

Method 5. Polyacylcarbodiimides from Bis(Acylcyanamids) and Diacid Chlorides

Properties of Polycarbodiimides

D. Azo Linkage Formation During Polymerization

Method 1. Oxidative Coupling of Aromatic Diamines

Method 2. Polyrecombination of Diamines

Method 3. Reduction of Bis(Diazonium) Compounds

Method 4. Reactions of Bis(Diazonium) Compounds

Method 5. Thermal Decomposition of Bis(Nitrosoamides)

Method 6. Decomposition of Bis(Chloroimides)

Properties of Azo Polymers

E. Nitrogen-Phosphorus Double Bond-Forming Polymerizations

Method 1. Polymerization of Diphosphines with Bis(Azides)

Table 1.1. Poly(Schiff Bases)

Table 1.2. Polyazines and Other Hydrazine-Derived Polymers

Table 1.3. Carbon-Nitrogen Double-Bond Containing Polymers

Table 1.4. Poly Carbodiimides

Table 1.5. Azo Polymers


Chapter II. Rings Containing Two Carbon Atoms

A. Poly(1,3,2-diazaboroles), Poly(1,3,2-oxazaboroles), and Poly(1,3,2-dioxaboroles)

Method 1. Polymerization of Bis(1,2-diamines) with Diboronic Acids

Method 2. Polymerization of Bis(1,2-diamines) with Tetraaminodiborons

Method 3. Miscellaneous Boron-Nitrogen Ring-Containing Polymers Poly(1,3,2-Oxazaboroles)

Method 4. Polymerization of Bis(aminophenols) with Diboronates

Method 5. Polymerization of Bis(aminophenols) with Tetraaminodiborons

Method 6. Miscellaneous Boron-Oxygen-Nitrogen Ring Polymerizations Poly(1,3,2-Dioxaboroles)

Method 7. Polymerization of Polyphenols with Diboronic Acids

Method 8. Polymerization of Tetraphenols with Tetraaminodiborons

Method 9. Miscellaneous 1,3,2-Dioxaboron Ring-Forming Polymerizations

B. Poly(1,3,2-diazaphospholes)

Method 1. Polymerization of Bis(phosphonic Acid Diamides) with Aromatic Tetraamines

Method 2. Polymerization of Aromatic Tetraamines with Phenyl Esters of Phosphorus Acids

C. Poly(1,3-diaza-2-silacyclopentanes)

Method 1. Reaction of Amines with Halo- or Aminosilanes

Method 2. Polymerization of Aromatic Amines with Silicon Tetrafluoride

D. Poly(1,2-oxazetidines)

Poly(1 ,3,4-oxadiazoles)

Method 1. Dehydration of Polyhydrazides

Method 2. Polymerization of Hydrazine and Dihydrazides with Dicarboxylic Acid Derivatives

Method 3. Polymerization of Diacid Chlorides with Bis-(tetrazoles)

Method 4. Polyacylamidrazones as Precursors to Polyoxadiazoles

Poly(l ,2,4-oxadiazoles) and poly(l,2,5-oxadiazoles)

Method 5. Polymerization of Diacid Chlorides with Diamidoximes

Method 6. Polyoxadiazoles from Nitrile Oxides

Properties of Poly(1,3,4-thiadiazoles)

E. Polyoxadiazoles

F. Poly(1,3,4-thiadiazoles)

Method 1. Dehydration of Polyoxathiahydrazides

Method 2. Dihydro-Poly(1,3,4-thiadiazoles) from 1,3-Dipolar Additions

G. Polytriazoles

Method 1. Polymerization of Hydrazine with Dicarboxylic Acid Derivatives

Method 2. Polymerization of Dihydrazides and Bis(amidrazones) with Dicarboxylic Acid Derivatives

Method 3. Polymerization of Bis(imide Chlorides) with Bis-(Tetrazoles)

Method 4. Polytriazoles from Additional Polymeric Precursors

Method 5. Polytriazole Synthesis from Dipolar Addition Reactions

Properties of Polytriazoles

H. Poly(1,2,4,5-tetrazines)

Method 1. Polymerization of Diimino Diesters with Hydrazine

Method 2. Polytetrazines from Dipolar Addition Reactions

I. Poly(2,5-diborapiperazines) and Poly(2,5-dibora-2,5-dihydropyrazines)

Method 1. Polymerization of Diisocyanides with Triorganoborons

Table II. 1. Poly(1,3,2-diazaboroles)

Table II.2. Poly(1,3,2-oxazaboroles)

Table II.3. Poly(1,3,2-dioxaboroles) and Related Polymers

Table II.4. Poly(1,3,2-diazaphospholes)

Table II.5. Poly(1,3-diaza-2-silacyclopentanes)

Table II.6. Poly(1,3,4-oxadiazoles)

Table II.7. Poly(1,2,4-oxadiazoles), Poly(1,2,4-oxadiazolines),and Poly(1,2,5-oxadiazoles)

Table II.8. Poly(1,3,4-thiadiazoles)

Table II.9. Poly(1,2,4-triazoles)

Table 11.10. Poly(1,2,3-triazoles)

Table 11.11. Poly(1,2,4,5-tetrazines)

Table 11.12. Poly(2,5-diborapiperazines) and Poly(2,5-dibora- 2,5-dihydropyrazines)


Chapter III. Rings Containing Three Carbon Atoms

A. Polyisoxazoles and Related Polymers Polyisoxazoles


Method 1. Polyisoxazoles from Dinitrile Di-N-oxides and Diacetylenes

Method 2. Polyisoxazolines from Dinitrile Di-N-oxides and Diolefins

Method 3. Polyisoxazolidines from Bis(nitrones) and Diolefins


Method 4. Polyoxazoles from o-Aminophenols and Carboxylic Acids

Method 5. Polyamides as Precursors to Polyoxazoles

Method 6. Polyesters as Precursors to Polyoxazoles

Method 7. Polyoxazoles from o-Aminophenols and Carboxylic Acid Anhydrides

Method 8. Polyoxazoles from Bis(o-Chloroamines)

Properties of Polyoxazoles


Method 9. Polyoxazolidones from Diisocyanates and Diepoxides

Method 10. Miscellaneous Additional Syntheses of Polyoxazolidones

Properties of Polyoxazolidones

B. Polythiazoles

Method 1. Polythiazoles from o-Mercaptoamines and Carboxylic Acids

Method 2. Polythiazoles from Bis(thioamides) and Bis(α-Haloketones)

Method 3. Polyamides as Precursors to Polythiazoles

Method 4. Polythiazoles from Sulfur and Toluidines

Properties of Polythiazoles

C. Polyimidazoles and Related Polymers Polyimidazoles

Method 1. Polyimidazoles from Dialdehydes and Bis(α-Diketones)

Method 2. Polyimidazoles from o-Diamines and Carboxylic Acids

Method 3. Polyimidazoles from o-Diamines and Carboxylic Acid Esters

Method 4. Polyimidazoles from o-Diamines and Carboxylic Acid Anhydrides

Method 5. Polymeric Precursors to Polyimidazoles

Method 6. Miscellaneous Syntheses of Polyimidazoles

Properties of Polyimidazoles


Method 7. Two-Step Synthesis of Polypyrrones from Tetracarboxylic Acid Derivatives and Tetraamines

Method 8. Direct Synthesis of Polypyrrones in Polyphosphoric Acid

Properties of Polypyrrones


Method 9. Polyimidazolines from o-Diamines and Dicarbonyl Compounds

Method 10. Polyimidazolines from Poly(ethyleneamines) and Cyanogen and Derivates

Method 11. Polyimidazolines from Poly(Amino Amides) Polyimidazolidones

Method 12. Polyimidazolidones from Vic-Diisocyanates Polyimidazolidiones

Method 13. Polyimidazolidiones from Diglycinates and Diisocyanates

Method 14. Polyimidazolidiones from Polymer Precursors

Method 15. Poly(5-iminoimidazolidiones) from Diisocyanates and Hydrogen Cyanide

Properties of Polyimidazolidiones

D. Polypyrazoles

Method 1. Polymerization of Tetracarbonyl Compounds with Dihydrazines or Dihydrazides

Method 2. Polypyrazoles from 1,3-Dipolar Addition Reactions

Method 3. Polymerization of Bis(diazo) Compounds with Diacetylenes

Properties of Polypyrazoles

E. Polytriazines

Method 1. Nitrile Trimerization-Polymerization to Polytriazines

Method 2. Polytriazines via Amidine Intermediates

Method 3. Trimerization of Isocyanates

Method 4. Poly(as-Triazines) from Polymerization of Bis-(Hydrazidines) and Bis(α-Diketones)

Properties of Polytriazines

Table III.1. Polyisoxazoles, Polyisoxazolines, and Polyisoxazolidines

Table III.2. Polyoxazoles

Table III.3. Polyoxazolidones

Table III.4. Polythiazoles

Table III.5. Polyimidazoles and Polybenzimidazoles

Table III.6. Polypyrrones

Table III.7. Polyimidazolines

Table III.8. Polyimidazolidones

Table III.9. Polyimidazolidiones

Table III.10. Polypyrazoles

Table III.11. Polypyrazolines

Table III.12. Polytriazines


Supplementary Reference List

Author Index Subject Index


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© Academic Press 1972
Academic Press
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About the Author

Robert Cotter

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