Semi-annual report of Schimmel & Co(Fritzsche Brothers) . esof Deussen2) have shown caryophyllene to consist of a mixture of severalhydrocarbons, it was not an easy matter to elucidate the structure of thisbody. The proneness of caryophyllene to inversion renders its investigationextraordinarily difficult. For example, the authors look upon the compoundC14H22O, which was obtained by Deussen and by Haarmann3) in the courseof oxidation with permanganate of potassium, as being not a derivative ofthe original caryophyllene, but a product of inversion, possibly of tricyclictsocaryophyllene. The onl
Semi-annual report of Schimmel & Co(Fritzsche Brothers) . esof Deussen2) have shown caryophyllene to consist of a mixture of severalhydrocarbons, it was not an easy matter to elucidate the structure of thisbody. The proneness of caryophyllene to inversion renders its investigationextraordinarily difficult. For example, the authors look upon the compoundC14H22O, which was obtained by Deussen and by Haarmann3) in the courseof oxidation with permanganate of potassium, as being not a derivative ofthe original caryophyllene, but a product of inversion, possibly of tricyclictsocaryophyllene. The only method by which useful results can be expectedis oxidation with ozone, and as a matter of fact, Semmler and Mayer havesucceeded, by gradually oxidising caryophyllene by means of ozone, inobtaining bodies which are in the main derived from two they call and , and they assignto them for the present two formula? which are analogous to those ofterpinolene and limonene, as follows: — H3CC CH2 CH3. H2C CH3 *) Berl. Berichte 44 (1911), 3657. 2) Comp. Report November 1908, 176; April 1909, 124; 3) Comp. Report October 1909, 177. CH CH3 1909, 177; April 1910, 169. - 175 — } In the course of the ozonising process acid and neutral decompositionproducts were obtained. Among the former was a ketocarboxylic acid,CnHisOs (b. p. 183 to 187° at 11,5 mm.; m. p. of the semicarbazone 183°),and a diketocarboxylic acid C14H22O4 (b. p. 229 to 232° at 11,5 mm.). Theneutral decomposition products consisted of a ketone Ci0Hi8O (b. p 73 to76° at 11,5 mm.; m. p. of the semicarbazone 176°), a diketone Ci2H2o02(b. p. 137 to 142° at 9 mm.; m. p. of the semicarbazone 219°) and a diketo-aldehyde Ci4H2203 (b. p. 181 to 184° at 13 mm.). When oxidised withnitric acid the ketocarboxylic acid CiiHi803 yielded a dicarboxylic acidC9H14O4, b. p. 222 to 225° (13 mm.) to which the authors give the na
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