. American chemical journal . sh the character of thesecond ring and to locate the remaining groups it was necessaryto introduce a hydrocarbon residue in place of bromine orethoxyl. This was accomplished with ethylmagnesium bromidewhich reacts with the bromide in accordance with the equation C,tR,,Bx + C2H5MgBr = C27H1AH5 + MgBr2. The hydrocarbon resulting from this reaction gives only one product when oxidized with chromic acid at the ordinary temperature—a diketone with all the hydrocarbon residues intact. On further oxidation in boiling acetic acid, the dike- Triphenylindene and Some of Its
. American chemical journal . sh the character of thesecond ring and to locate the remaining groups it was necessaryto introduce a hydrocarbon residue in place of bromine orethoxyl. This was accomplished with ethylmagnesium bromidewhich reacts with the bromide in accordance with the equation C,tR,,Bx + C2H5MgBr = C27H1AH5 + MgBr2. The hydrocarbon resulting from this reaction gives only one product when oxidized with chromic acid at the ordinary temperature—a diketone with all the hydrocarbon residues intact. On further oxidation in boiling acetic acid, the dike- Triphenylindene and Some of Its Derivatives. 219 tone gives o-dibenzoylbenzene. These results show that thehydrocarbon is a derivative of 1,2,3-triphenylindene:CjHj C5H5 \/ / .CCeH^ V^ , \/ The bromide C27H29Br is therefore i-brom-1,2,3-triphenylin-dene and it is evident that there must be a shifting of thebromine atom when a-bromtriphenylpropiophenone loseswater and passes into the indene derivative: C-C,H3 /\ /l\ /Br(C,H,),CHCBr(CeHJC0C,H5. It is remarkable that a change so complicated as this oneshould take place far below the melting point of the bromo-ketone, and without more than a trace of by-products. I havemade a number of experiments for the purpose of determining 220 Kohler. to what extent this reaction can be used for making otherindene derivatives and have found that the reaction does nottake place either with the ketone that has hydrogen in placeof bromine, or with bromoketones that have hydrogen or alkylin place of any of the phenyl groups in bromtriphenylpropio-phenone. By starting with bromtriphenylindene it is easy to gettriphenylindene itself as well as a number of derivatives thatare of interest in connection with recent investigations ofsubstances that are rich in phenyl groups. The hydrocarbonbehaves almost exactly like triphenylmethane. The singlehydrogen atom attached to the indene ring is readily replacedboth by halogens and by potassium. The hydrocarbon canbe oxidized
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