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• W1900810366 abstract "Abstract Arenediazonium, ArN 2 + , ions may function as Lewis acids reacting with nucleophiles (Lewis bases, Nu − or NuH followed by loss of a proton) to give covalently bonded adducts, ArN 2 ‐Nu, at the β‐nitrogen of the arenediazonium ion, which is the electrophilic reactive center. Typical examples of covalently bonded adducts are the azo dyes (C‐coupling) but atoms other than C may be involved and the present chapter will mainly focus on the chemistry of O‐coupling adducts of the type ArN=N‐Nu, e.g., where Nu = OH − (formation and decomposition of diazohydroxides and diazoates), Nu = RO − , ArO − , ROH and cyclodextrins (formation and decomposition of diazoethers), with special emphasis on the kinetics and mechanism of the reactions involved. We will also cover, to a lower extent, those reactions with other nucleophiles leading to S‐, N‐ and P‐adducts. O‐coupling reactions are complicated by two major features. First, the formed adducts may display geometrical isomerism, leading to the E ‐( syn ) and Z ‐( anti ) forms, which show different stability and can be interconverted to each other by acid catalyzed processes. Second, some of the O‐adducts formed may be, in turn, components of a Lewis acid‐base equilibrium, for example between ArN 2 + and OH − ions, and hence may undergo further reactions." @default.
• W1900810366 created "2016-06-24" @default.
• W1900810366 creator A5040911965 @default.
• W1900810366 date "2010-10-15" @default.
• W1900810366 modified "2023-10-18" @default.
• W1900810366 title "Diazohydroxides, Diazoethers and Related Species" @default.
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• W1900810366 doi "https://doi.org/10.1002/9780470682531.pat0511" @default.
• W1900810366 hasPublicationYear "2010" @default.
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