Diazoethers

Alkyl and aryl arenediazoates ( diazoethers ) are generally unstable and even explosive compounds. They are produced by interaction of alcohols with (explosive) bis(arenediazo) oxides, or of -blocked phenols with diazonium salts. The thio analogues are similar. Individually indexed compounds are ... 

Diaza-2-boracycloalkanes, 93 Diazirines, 93 Diazoazoles, 94 Diazo compounds, 94 Diazoethers, 96 Diazomethane salts, 96 Diazonium carboxylates, 96 Diazonium perchlorates, 96 Diazonium salts, 97 Diazonium sulfates, 98 Diazonium sulfides and derivatives, 99 Diazonium tetrahaloborates, 100 Diazonium triiodides, 101 a-Diazo-/J-oxosulfones, 102 Diazotisation, 102... 

Theoretical calculations and studies do not appear to have been carried out on any of these ring systems. However, the instability of 3,1,2-benzoxadiazines has been discussed in terms of their formulation as examples of cyclic 5yn-diazoethers <88IJC(B)653>. 

Diazoethers, diazoisothiouronium salts, and sulfonium salts from diazonium salts s. 17, 150... 

During the main period of development a large number of redox systems were investigated. As reductant, in approximate order of development, were diazoether, sugar-iron pyrophosphate, polyamine and sodium formaldehyde sulphoxylate. Amongst the peroxides cumene and p-menthane hydroperoxides have found favour. The SFS system based on sodium formaldehyde sulphoxylate has been particularly useful because of its low cost, ease of preparation and reproducibility. A simplified mechanism for the initiation stage may be given as ... 

Bravo Diaz, C. Diazohydroxides, diazoethers and related species, in Patai s Chemistry of Functional Groups The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids, Z. Rappoport, J. F. Liebman (Eds.), Vol. 2, p. 853, J. Wiley Sons, Chichester, UK, 2011. 

Fernindez-Alonso, A. and C. Bravo-Diaz. Methanolysis of 4-bromobenzenediazonium ions. Effects of acidity, [MeOH] and temperature on the formation and decomposition of diazoethers that initiate homolytic dediazoniation. Org. Biomol. Chem 6, 2008 4004-4011. 

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