By Heinrich Zollinger
Diazo compounds play a tremendous function as response intermediates and reagents in natural synthesis. This booklet is a serious, good- referenced and eminently readable creation to the chemistry of aliphatic, inorganic and organometallic diazo compounds. It presents well-researched info which can rather be acquired in simple terms through expensive and time-consuming searches of multi-volume treatises and the unique literature. subject matters lined extensive contain: - education 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 ebook a hugely precious reference paintings for man made natural chemists, inorganic chemists, organometallic chemists and business chemists. Already to be had: quantity 1 of Diazo Chemistry overlaying fragrant and heteroaromatic compounds.
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Additional info for Diazo Chemistry, Vol. 2, Aliphatic, Inorganic and Organometallic Compounds
Aryldiazomethanes (Ar —CH = N2) are readily prepared by exposure of the arenecarbaldehyde tosylhydrazone to base (Dudman and Reese, 1982). The pink-red naphthalen-1-yldiazomethane, for instance, is obtained by addition of sodium methoxide to a suspension of 1-naphtaldehyde 4-toluenesulfonyl hydrazone in methanol. , 1983). A surprisingly high yield of 98% was reported by Just et al. (1988) for the Bamford-Stevens synthesis of bis(4-nitrophenyl)-diazomethane, using 1 M NaOH at 75 °C (3 h). , 1965) showed that the Bamford-Stevens reaction can be exploited in vacuo instead of in solution.
205). Summarizing the work accomplished on the synthesis of aliphatic diazo compounds by nitrosation of aminoalkanes, it has to be emphasized that precaution is absolutely necessary in its application. , amino-a,a'-dicarbonyl compounds), the results are unreliable for most classes of amines. This method is not recommended if the specific compound has not been described so far in the literature, or if another method (see Sects. 6) is available. We add here a short discussion of another method for diazotization of aliphatic amines, although it is not suitable for the generation of diazoalkanes.
4) a related diazomethane synthesis (depicted many decades ago by Staudinger) will be added, although it is not strictly related to this section. From the synthetic point of view, it is not particularly interesting, but mechanistically it is worthy of discussion because nitrilimine, an isomer of diazomethane, is probably formed as a steady-state intermediate in this reaction. 1 Dehydrogenation of Hydrazones Curtius discovered both the first synthetic route to aliphatic diazo compounds by nitrosation of amines (1883, see Sect.
Diazo Chemistry, Vol. 2, Aliphatic, Inorganic and Organometallic Compounds by Heinrich Zollinger