Zincke; and his researches have led to the discovery of many chlorinated oxidation products which admit of decomposition into cyclic compounds containing fewer carbon atoms than characterize the benzene ring, and in turn yielding openchain or aliphatic compounds.
Decompositions of this nature were first discovered in the naphthalene series, where it was found that derivatives of indene (and of hydrindene and indone) and also of benzene resulted; Zincke then extended his methods to the disintegration of the oxybenzenes and obtained analogous results, R-pentene and aliphatic derivatives being formed (Rsymbolizing a ringed nucleus).
Zincke and 0.
Our knowledge of the chemical structure of the monosaccharoses may be regarded as dating from 1880, when Zincke suspected some to be ketone alcohols, for it was known that glucose and fructose, for example, yielded penta-acetates, and on reduction gave hexahydric alcohols, which, when reduced by hydriodic acid, gave normal and secondary hexyliodide.
Zincke (Ber., 1883,16, p. 2929; 1884, 1 7, p. 3026; 1887, 20, p. 3171) and R.
Zincke found that the products obtained by coupling a diazonium salt with a-naphthol, and by condensing phenylhydrazine with a-naphthoquinone, were identical; whilst Meldola acetylated the azophenols, and split the acetyl products by reduction in acid solution, but obtained no satisfactory results.
Zincke, Berichte,1871, 4, p. 57 6).
Zincke, Ber., 1886-1894; A.
Zincke, Ber., 1887, 20, p. 1267).
The ring of this compound is ruptured by caustic soda with the formation of perchlorvinyl acrylic acid (5), which gives on reduction ethidine propionic acid (6), a compound containing five of the carbon atoms originally in the benzene ring (see Zincke, Ber., 18 94, 27, p. 33 6 4) (the carbon atoms are omitted in some of the formulae).
Zincke, ib., 1895, 28, p. 3121); by the action of sulphuric acid on para-substituted phenylhydroxylamines (E.