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Diazo chemistry. 1, Aromatic and heteroaromatic compounds

Author: Heinrich Zollinger
Publisher: Weinheim ; Cambridge : VCH, ©1994.
Edition/Format:   Print book : EnglishView all editions and formats

This text provides a homogenous presentation of aspects of diazo chemistry. It is practice-oriented due to a strong emphasis on applications and includes many tables, schemes and literature  Read more...


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Material Type: Internet resource
Document Type: Book, Internet Resource
All Authors / Contributors: Heinrich Zollinger
ISBN: 1560818786 9781560818786 3527292136 9783527292134
OCLC Number: 60241197
Description: [1 volume]
Contents: Part 1 Introduction: history of aromatic and heteroaromatic diazo compounds; nomenclature; general references. Part 2 Methods for the preparation of aromatic and heteroaromatic diazo compounds: diazotization of amines with alkali nitrite in dilute aqueous mineral acids; diazotization in concentrated mineral acid; isolation of diazonium salts; diazotization of 2- and 4-aminophenols; formation of diazonium salts under anhydrous conditions; other reactions involving formation of aromatic diazonium ions. Part 3 Kinetics and mechanism of diazotization: historical development; influence of acidity on the rate and mechanism of diazotization in aqueous sulfuric and perchloric acids; nucleophilic catalysis of diazotization; transformation of the N-Nitrosoamine intermediate into the diazonium ion. Part 4 The structure of diazonium compounds: introductory remarks; structure of arenediazonium salts; theoretical investigations. Part 5 Acid-base and isomerization reactions of diazo compounds in water: the aromatic diazonium ion as a dibasic acid; the combined system of acid-base addition, (Z)/(E)- and prototropic isomerization reactions of arenediazonium ions; kinetics and equilibria of arenediazonium ions in water. Part 6 Additions of other nucleophiles to arenediazonium ions: O-Coupling; S-coupling; N-coupling; P-coupling; C-coupling; intramolecular coupling. Part 7 Structural and mechanistic aspects of additions of nucleophiles to diazonium ions: (Z)/(E)-isomerism; investigations on reactivities by the interpretation of substituent effects - the Hammett and related equations; the electronic influence of the diazonio group as a substituent; influence of substituents on the addition of nucleophiles to arenediazonium ions. Part 8 Dediazoniation of arenediazonium ions: introduction to dediazoniation in general; multiplicity of pathways and products; the D[N] + A[N] mechanism of dediazoniation; molecular orbital investigations on heterolytic dediazoniations and on aryl cations; dediazoniations via aryne intermediates; dediazoniation initiated by an electron transfer; solvent effects in competitive homolytic and heterolytic dediazoniation; dediazoniation in alkaline aqueous solutions; dediazoniation in highly nucleophilic solvents and in the presence of good nucleophiles; dediazoniation in alcohols. Part 9 Logic, psychology, and serendipity of scientific discoveries - an interlude. Part 10 Applications of heterolytic and homolytic dediazoniations in organic syntheses: hydro-de-diazoniation; hydroxy- and mercapto-de-diazoniations and related reactions; fluoro-de-diazoniation; chloro-, bromo-, and cyano-de-diazoniations - the Sandmeyer reaction; iodo-de-diazoniation and related reactions; azido-de-diazoniation; dediazoniation in the presence of carbonyl, sulfonyl, and related compounds; replacement of the diazonio group by alkenes and alkynes - the Meerwein reaction; arylation of aromatic compounds - the Gomberg-Bachmann and related reactions. (Part contents).
Responsibility: Heinrich Zollinger.


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