By Prof. Dr. Drs. h. c. Heinrich Zollinger(auth.)
Diazo compounds play a tremendous function as response intermediates and reagents in natural synthesis. This e-book is a severe, good- referenced and eminently readable advent to the chemistry of aliphatic, inorganic and organometallic diazo compounds. It offers well-researched details which could rather be received simply by means of expensive and time-consuming searches of multi-volume treatises and the unique literature.
issues coated intensive include:
- guidance and constitution of diazo compounds
- kinetics and mechanism of diazotizations
- reactions of diazo compounds
- purposes in natural synthesis
- steel complexes with diazonium and diazo compounds
Many tables and response schemes in addition to copious literature citations make this booklet a hugely worthwhile reference paintings for artificial natural chemists, inorganic chemists, organometallic chemists and commercial chemists.
Already on hand: quantity 1 of Diazo Chemistry masking fragrant and heteroaromatic compounds.
Chapter 1 creation (pages 1–10):
Chapter 2.1–2.5.2 tools for the practise of Alkane, Alkene, and Alkyne Diazo Compounds: part 2.1–2.5.2 (pages 11–45):
Chapter 2.5.3–2.11 equipment for the education of Alkane, Alkene, and Alkyne Diazo Compounds: part 2.5.3–2.11 (pages 46–94):
Chapter three Inorganic Diazo Compounds and steel Complexes with Dinitrogen as Ligand (pages 95–119):
Chapter four Kinetics and Mechanism of Aliphatic Diazotization (pages 121–143):
Chapter five The constitution of Aliphatic Diazo Compounds (pages 145–189):
Chapter 6 Reactions of Aliphatic Diazo and Diazonium Compounds now not concerning preliminary Dediazoniation (pages 191–240):
Chapter 7.1–7.4 Dediazoniation Reactions related to Diazonium Ion Intermediates: part 7.1–7.4 (pages 241–277):
Chapter 7.5–7.8 Dediazoniation Reactions related to Diazonium Ion Intermediates: part 7.5–7.8 (pages 278–304):
Chapter 8.1–8.5 Dediazoniation Reactions related to Carbene and Carbenoid Intermediates: part 8.1–8.5 (pages 305–344):
Chapter 8.6–8.8 Dediazoniation Reactions regarding Carbene and Carbenoid Intermediates: part 8.6–8.8 (pages 344–381):
Chapter nine Miscellaneous Reactions related to Diazo and comparable Compounds (pages 383–419):
Chapter 10 steel Complexes of Diazonium and Diazo Compounds (pages 421–454):
Chapter eleven Epilogue: From Peter Griess' Discovery to Organometallic Diazo Compounds (pages 455–458):
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Additional resources for Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds
26 2 Methods for the Preparation of Alkane, Alkene, and Alkyne Diazo Compounds Acylated or sulfonated a-amino ketones are smoothly converted to the corresponding a-diazoketones. Open-chain diazo-a,a'-dicarbonyl compounds form complexes with boron trifluoride. There are two types of such complexes, as shown by Fahr and Hormann (1965) by means of IR spectra. 35). They also undergo a reaction typical of solid aromatic diazonium salts, namely the Balz-Schiemann reaction (see Zollinger, 1994, Sect. 36 is formed (2-12) (Prim and Schank, 1978).
39. ), possess a mesomeric (zwitterionic) phenolate-diazonium and quinone-diazide structure. We discussed these structures in the context of aromatic diazotization (Zollinger, 1994; Sect. 4) because the synthetic methods used are closely related to those used for aromatic diazonium salts. This is also the case for the diazotization of amino-di-, tri- and tetrazoles, which, in their neutral form, contain a heterocyclic NH group in the yff-position to the amino group. After diazotization, the NH group is very acidic.
For these compounds, of the three major routes starting from 1,2-dialkylated or 1,2-diarylated ethanones (Scheme 2-26), Hauptmann and Wilde (1969) demonstrated that pathway B is widely applicable. , 1965). 72 (for the stoichiometry, see Scheme 2-27). For the dehydrogenation to the a-diazo ketone, MnO2 in chloroform is used. 71 RCOCOR nvywwi ILJI ri i iwwwi n i RCOCHBrR' + 3 H2N — NH2 ^ lf. \ (2-26) RCOCR' + H2N — NH3Br + 2 NH3 (2-27) NNH2 method, Hauptmann's group synthesized 37 a-diazo ketones, among them nine previously unknown.
Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds by Prof. Dr. Drs. h. c. Heinrich Zollinger(auth.)