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 serious, good- referenced and eminently readable creation to the chemistry of aliphatic, inorganic and organometallic diazo compounds. It offers well-researched details which may rather be received in basic terms by way of expensive and time-consuming searches of multi-volume treatises and the unique literature.
issues coated extensive include:
- training and constitution of diazo compounds
- kinetics and mechanism of diazotizations
- reactions of diazo compounds
- functions 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 priceless reference paintings for artificial natural chemists, inorganic chemists, organometallic chemists and business chemists.
Already on hand: quantity 1 of Diazo Chemistry overlaying fragrant and heteroaromatic compounds.
Chapter 1 advent (pages 1–10):
Chapter 2.1–2.5.2 tools for the coaching 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 training 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 no longer related to preliminary Dediazoniation (pages 191–240):
Chapter 7.1–7.4 Dediazoniation Reactions regarding Diazonium Ion Intermediates: part 7.1–7.4 (pages 241–277):
Chapter 7.5–7.8 Dediazoniation Reactions concerning Diazonium Ion Intermediates: part 7.5–7.8 (pages 278–304):
Chapter 8.1–8.5 Dediazoniation Reactions concerning Carbene and Carbenoid Intermediates: part 8.1–8.5 (pages 305–344):
Chapter 8.6–8.8 Dediazoniation Reactions concerning Carbene and Carbenoid Intermediates: part 8.6–8.8 (pages 344–381):
Chapter nine Miscellaneous Reactions related to Diazo and similar 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 info for Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds
In the reaction sequence C, introduction of the formyl group by a Claisen ester condensation with a formic acid ester is followed by treatment with 4-toluenesulfonyl azide, i. , by a diazo transfer reaction (Regitz and Menz, 1968; see Sect. 6). , 1988 and references therein). Silver oxide and silver carbonate have the advantage of a higher rate of reaction with hydrazones relative to mercury(n) oxide. Therefore, these reagents are mainly used for the synthesis of labile diazoalkanes. Ag2O is, for example, suitable for the dehydrogenation of cyclohexanone hydrazone to give diazocyclohexane (2-28), whereas with HgO, the main product is di(cyclohexyl)azine (Heyns and Heins, 1957).
As shown in D, an arylsulfenyl chloride (Ar = 2-nitrophenyl) is used, which forms a sulfenylhydrazone as intermediate. , 1975). So far as we can see, this method has not been used again, probably because of the instability and poor availability of sulfenyl chlorides. The Bamford-Stevens sequence of reactions was used first by Borsche and Frank (1926), but its synthetic potential was discovered only 26 years later by Bamford and Stevens (1952) and was subsequently applied by many chemists. Aryldiazomethanes (Ar —CH = N2) are readily prepared by exposure of the arenecarbaldehyde tosylhydrazone to base (Dudman and Reese, 1982).
1966). Miller (1959) proposed the mechanism (2-24) for the dehydrogenation, explaining the role of the potassium ethanolate in deprotonating the mercury-hydrazone complex. Mechanism 2-24 is difficult to understand on the basis of observations made by Droescher and Jenny (1968). These authors mentioned that well crystallized, very pure HgO is not active for dehydrogenation of hydrazones. When a Guinier-Preston diagram * of very pure HgO was compared with that of a sample that was activated * The Guinier-Preston technique is an X-ray method that allows detection of atoms of higher mass on solid surfaces.