Nomenclature and General References

Methylene ( CH2), the parent carbene, was already considered by Nef (1895, p. 359) to exist. Better evidence was found by Staudinger and Kupfer (1912) in the reaction of diazomethane with carbon monoxide, yielding ketene (1-6). 

Staudinger s historical merits for our knowledge of diazoalkanes, based on his work between 1911 and 1921, became somewhat overshadowed by his later and clearly more fundamental and pioneering ideas about the formation and structure of macromolecules (Nobel Prize 1953). It should be emphasized, however, that his development of the concept of polymerization was, at least in part, based on his observations of the formation of polymethylene in the dediazoniation of diazomethane. Macromolecular chemistry, therefore, appears to be a child of early diazo chemistry  

It is also appropriate to mention the modern mechanistic work on the very first type of reaction in the chemistry of aliphatic diazo compounds, namely deamination (1-1). In contrast to the 1,3-dipolar cycloadditions deaminations of aliphatic amines are relatively seldom applied for synthetic purposes (see Sect. 7.7), because they lead in most cases to a mixture of nucleophilic substitution products as well as elimination and rearrangement products. It has been clear, at least since the work of Young and Andrews (1944), Ingold s group (Brewster et al., 1950) and others, that, basically, these reactions belong to the class of nucleophilic aliphatic substitutions in spite of a bewildering number of complicating factors (see Chapt. 7). 

This fairy-tale is a fancy background of Diazo Chemistry I and II  

We emphasized in the Preface that the subject of this book and of that on aromatic diazo compounds (Zollinger, 1994) are closely related, but that the two books are independent. As a consequence, it should be possible to read one of the books without frequent consultation of the other. Strict adherence to that policy would force the 

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