No abstract

a . o-Diphenylparaffins, with the exception of 1 : 2diphenylethane, can be obtained in good yield by the F i t t i g reaction between bromobenzene, sodium and the corresponding a. wdibromoparaffin. With 1 : IOdibromodecane higher diphenylparaffins are also formed. F i t t i g reaction depends on the fact that the aromatic halogenide reacts more quickly with sodium than the aliphatic halogenide, but the aliphatic halogenide reacts more quickly with the aromatic sodium derivative than the aromatic halogenide 2). l) J. v a n A 1 p h en, This Journal 59, 32 (1940).

The methyl esters of fumaric add as well as of maleic add combine with diphenyldiazomethane to give the same pyrazoline derivative, which upon being heated splits off nitrogen and gives the methyl ester of trans-1 ,l-dlphenyl-cyclopropane dicarbonic add-2.3. When maleic acid anhydride is made to combine with diphenyl diazomethane a compound is formed which splits off nitrogen rapidly at 80-90' and slowly at ordinary temperatures, giving the anhydride of cis-1.1 diphenylcyclopropane dicarbonic acid-2,3.

By the addition of diphenyldiazomethane to the methyl esters of acetylene dicarbonic acid, of phenyl propiolic acid and of propiolic acid, pyrazolenines are formed, which, under different circumstances and with a migration of several groups. undergo a rearrangement into pyrazoles.

When indigo was nitrated with absolute nitric acid, either directly or dissolved in sulphuric acid or acetic acid only decomposition products, containing nitrated isatins, could be obtained. but when indigo was nitrated in acetic anhydride, well defined products could be prepared. These were derivatives of 2-acetoxy-3 : 3'diketc+diindolinyl-2 : 2' into which one, two or three nitro groups were introduced, depending on the amount of nitric acid used. On heating. these compounds split off a molecule of acetic acid and mono-, di-, or tri-nitroindigos remained behind. An analogous result was obtained, when indigo was nitrated in butyric anhydride. Indigo could also be nitrated in acetyl chloride but 5-chloroisatin was then obtained.