By Heinrich Zollinger
Diazo compounds play an immense position as response intermediates and reagents in natural synthesis. This ebook is a serious, good- referenced and eminently readable creation to the chemistry of aliphatic, inorganic and organometallic diazo compounds. It presents well-researched details that may rather be received simply by means of high priced and time-consuming searches of multi-volume treatises and the unique literature. themes coated extensive comprise: - guidance 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 ebook a hugely invaluable reference paintings for man made natural chemists, inorganic chemists, organometallic chemists and commercial chemists. Already to be had: quantity 1 of Diazo Chemistry masking fragrant and heteroaromatic compounds.
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Additional info for Diazo Chemistry, Vol. 2, Aliphatic, Inorganic and Organometallic Compounds
H xN2 ~ C ~~ C \ (1) H (6) (7) — C~ d > + N3S02Arc) C=O + J^C=N2 H (*) ^C=CC^ + ^C=N2 (9) RCOC1 + «», "^C=^N22 R-C' + OH~ II 0 H ^C=N2 1 2 c2 ^ ~h" \ N ° -^ R— C 1I I1 0 + HC1 2 -*> ^C=N2 + ROXT H 1 a ) Number of syntheses described in detail in Organic Syntheses, Coll. Vol. I- VIII (1932-1994) and Vol. 70-71 (1992-1993). b ) Ox = metal oxides and various other oxidants for hydrazone oxidation. c ) Ar = 4-CH3C6H4 in most cases. d ) Or a precursor of a carbanion. The diazo transfer method 6 is also used for aromatic diazonium salts (see Zollinger, 1994, Sect.
These ions alkylate desoxynucleic acids. This alkylation is the cause for the carcinogenicity of the 7V-nitrosodi- and -monoalkylamines, which is discussed in more detail in the context of the chemistry of nitroso amines (Sect. 2). The Nnitroso derivatives of primary amines are precursors of the aromatic and aliphatic diazonium ions. 6 7V-nitroso compounds of secondary aliphatic amines undergo enzymatic reactions in living organisms in which carbocations are ultimately formed. Therefore, method 2 for diazoalkane syntheses in Table 2-1 is, in principle, questionable, because the 7V-nitroso compounds required are toxic.
Usually, equimolar amounts of amine, HC1 and NaNO2, or amine and NOC1, are used. A better alternative is nitrosation with pentyl nitrite in the presence of up to 30% acetic acid, as found by Takamura et al. (1975). Yields higher than 60% were obtained with aamino-substituted esters of some aliphatic carboxylic acids. The diazo compound is often extracted into an immiscible organic solvent as soon as it is formed. Searle (1963) recommends dichloromethane for the synthesis of diazoacetates, as CH2C12 has the ability to protect the diazo compound from decomposition caused by aqueous mineral acid.