By Heinrich Zollinger
Diazo compounds play a tremendous position as response intermediates and reagents in natural synthesis. This e-book is a severe, good- referenced and eminently readable creation to the chemistry of aliphatic, inorganic and organometallic diazo compounds. It offers well-researched info which can 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 contain: - practise 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 publication a hugely useful 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
67) takes place, as shown by Boyer and Goedel (1960). 64 are electrophilic and, therefore, able to react with nucleophilic centers. This type of reaction is successfully competitive with dediazoniation only if the nucleophilic center is very close. Indirectly, one can conclude that the dediazoniations in (2-23) have half-lives comparable to those of diffusion-controlled reactions. 67 Nowadays, hydrazone dehydrogenation with HgO is probably the synthetic method, next to cleavage of 7V-nitroso compounds, that is most frequently used for diazoalkanes substituted with alkyl, aryl, heteroaryl, or carbonyl groups.
Benzonitrile was used as solvent. This is rather surprising, considering the general experience on the effect of solvent polarity mentioned above. As acetic acid is formed when using lead(iv) tetraacetate, this dehydrogenation reagent can only be used for the synthesis of diazoalkanes with low acid sensitivity, i. , those containing electron acceptor substituents at the diazo Catom, such as CF3 (above), CN (diazomalonitrile, Ciganek, 1965 a), or phenylsulfonyl (Diekmann, 1963). Lead(iv) tetraacetate can be used only for the syntheses of substituted diazoalkanes with a low electron density at the C(a)-atom, which decreases the sensitivity to protonation.
Another synthesis of an aliphatic diazo compound in a two-phase system was reported by Moore and Arnold (1983). 16) in a mixture of dichloromethane and aqueous HC1 at 0 °C (2-6). The overall reaction is probably a diazotization followed by a hydroxy-de-chlorination and a hydroxyde-protonation. , 1960a)*. A solu* Metal-nitrosyl complexes can also be used for diazotizations at relatively high basicities, as discussed later in this section. 22 2 Methods for the Preparation of Alkane, Alkene, and Alkyne Diazo Compounds tion of NOC1 in anhydrous ether is added slowly to a three- to four-fold excess of methylamine (2-7) at -80°C.
Diazo Chemistry, Vol. 2, Aliphatic, Inorganic and Organometallic Compounds by Heinrich Zollinger