Effect of Substitution on the Dissociation of Hexaarylethanes. VII.¹ Meta and Para Phenyl Groups

Abstract

Vol. 61 tetrachloride solution. In the first the reaction was interrupted after six hours and, in the second, after twelve and a half hours. Both gave acidic fractions boiling from 90-180°( 1 mm.), but no pure product was isolated. The boiling point changed continuously. The ozonization was not complete in either case. The acidic fraction amounted to 2.1 g. boiling below 100°( 1 mm.) and 3.2 g. boiling from 100-180°( 1 mm.) with some residue, when the ozonization was carried out for twelve and a half hours. The acid fraction gave no 2,4-dinitrophenylhydrazone.Preparation of A11-Dodecahydro-9-phenanthrone.-This ketone was prepared by the formic acid cyclization of dicyclohexenylacetylene.48 The ketone was fractionated to give a fraction boiling at 135-136°( 2 mm.) with the refractive index n25d 1.5296. The refractive index of the sample did not vary during distillation.Hydrogenation of An-Dodecahydro-9-phenanthrone to Tetradecahydro-9-phenanthrol.-A solution of 22.2 g. of the ketone in 120 ml. of ethyl alcohol was hydrogenated at 185°under a pressure of 100-200 atmospheres of hydrogen using Raney nickel10 as the catalyst. Four hours were required for complete reduction to the saturated alcohol. The product from the hydrogenation was filtered and the solvent distilled. The residue was fractionally distilled through a modified Widmer column.The portion boiling at 136-138°( 2 mm.) solidified to a waxy solid on standing for a few hours. The product did not give a sharp melting point and it has not been possible to purify it by recrystallization. The wide