By Prof. Dr. Drs. h. c. Heinrich Zollinger(auth.)
Through the writer of colour Chemistry!
Diazo compounds play a massive position as response intermediates and reagents in natural synthesis. This booklet is a serious, good referenced and eminently readable creation to the chemistry of fragrant and heteroaromatic diazo compounds. It offers good researched info which can rather be got merely through expensive and time-consuming searches of multi-volume treatises and the unique literature.
subject matters lined intensive include:
* education and constitution of diazo compounds
* kinetics and mechanism of diazotizations
* reactions of diazo compounds
* purposes in natural synthesis
Many tables and response schemes in addition to copious literature citations make this booklet a hugely important reference paintings for man made natural chemists, commercial chemists and colour chemists.
additionally drawing close: quantity 2 of Diazo Chemistry masking aliphatic, inorganic and organometallic compounds.
Chapter 1 creation (pages 1–10):
Chapter 2 tools for the training of fragrant and Heteroaromatic Diazo Compounds (pages 11–37):
Chapter three Kinetics and Mechanism of Diazotization (pages 39–64):
Chapter four The constitution of Diazonium Compounds (pages 65–88):
Chapter five Acid–Base and Isomerization Reactions of Diazo Compounds in Water (pages 89–105):
Chapter 6 Additions of different Nucleophiles to Arenediazonium Ions (pages 107–141):
Chapter 7 Structural and Mechanistic features of additives of Nucleophiles to Diazonium Ions (pages 143–159):
Chapter 8.1–8.5 Dediazoniation of Arenediazonium Ions: Sections 8.1–8.5 (pages 161–188):
Chapter 8.6–8.10 Dediazoniation of Arenediazonium Ions: Sections 8.6–8.10 (pages 188–212):
Chapter nine good judgment, Psychology, and Serendipity of medical Discoveries – An Interlude (pages 213–219):
Chapter 10.1–10.9 functions of Heterolytic and Homolytic Dediazoniations in natural Syntheses: Sections 10.1–10.9 (pages 221–253):
Chapter 10.10–10.13 functions of Heterolytic and Homolytic Dediazoniations in natural Syntheses: Sections 10.10–10.13 (pages 253–288):
Chapter eleven Host–Guest Complexation of Arenediazonium Salts (pages 289–303):
Chapter 12.1–12.6 Azo Coupling Reactions: Sections 12.1–12.6 (pages 305–346):
Chapter 12.7–12.11 Azo Coupling Reactions: Sections 12.7–12.11 (pages 346–383):
Chapter thirteen Formation and Reactions of Triazenes (pages 385–404):
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Extra info for Diazo Chemistry I: Aromatic and Heteroaromatic Compounds
Research into the mechanism of diazotization was based on Bamberger's supposition (1894b) that the reaction corresponds to the formation of 7V-nitroso-7V-alkylarylamines. The 7V-nitrosation of secondary amines finishes at the nitrosoamine stage (because protolysis is not possible), but primary nitrosoamines are quickly transformed into diazo compounds in a moderately to strongly acidic medium. The process probably takes place by a prototropic rearrangement to the diazohydroxide, which is then attacked by a hydroxonium ion to yield the diazonium salt (Scheme 3-1; see also Sec.
They are also used for inhibiting the decomposition of diazonium ions in solution. , 1977) point to the formation of molecular complexes of the diazonium ions with the arenesulfonates rather than to diazosulfonates (ArN2 — OSO2Ar') as previously thought. For a diazonium ion in acetic acid/water (4:1) solutions of naphthalene derivatives, the complex equilibrium constants are found to increase in the order naphthalene < 1-methylnaphthalene < naphthalene1-sulfonic acid < 1-naphthylmethanesulfonic acid.
As discussed in Chapter 8, the dediazoniation of arenediazonium ions is either hetero- or homolytic. The homolytic mechanism is based on electron transfer from suitable donors. In the solid state, decomposition of a diazonium salt is therefore dependent on the donor properties of the anion: tetrafluoroborate is a (much) weaker donor than chloride. Bourdeaux et al. (1963) calculated electron affinities of complex metal anions MmC\™~n (n > m) and found the sequence Fe3+