TETRAPHENYLDISTIBYL 1025 hydroxide was poured into a large beaker, heated almost to the boiling point and stirred vigorously with a mechanical stirrer. 4-Toluenesulfonechloride was then added in small portions. A vigorous reaction ensued with each addition of the chloride. After all of the material had been added the clear solution was cooled, whereupon the amide precipitated. The latter was separated, dissolved in boiling water and treated with charcoal. After filtration the sulfonamide separated from the cold, concentrated solution in the form of colorless crystals.
N-Pentamethylene-S-triarylmethyldithiourethans are formed almost instantly and quantitatively from the interaction, at ordinary temperature, of a triarylmethyl halide and the piperidine salt of N-pentamethylenedithiocarbamic acid. These urethans are of interest because of the fact that they dissociate spontaneously, in solution, with the formation of triarylmethyls.3In view of the great reactivity of the halogen in diarylarsyl and diarylstibyl iodides it seemed probable that these halides, too, might react with the piperidine salt of N-pentamethylenedithiocarbamic acid similarly to the triarylmethyl halides. It was found that piperidine hydriodide was precipitated almost immediately upon the addition of diphenylarsyl iodide, dissolved in benzene, to the piperidine salt of the dithiocarbamic acid. A colorless, crystalline compound was isolated from the benzene solution which, according to the results obtained from an analysis and molecular weight determination, was N-pentamethylene-S-diphenylarsyldithiourethan.
Halogen in an organic compound is determined, usually, by the Carius2 or by the Lemp and Broderson3 modification of the Parr4 and Pringsheim5 methods.1 This investigation was made possible by a grant from the Faculty Research Fund of the University of Michigan.2 Carius, Ann., 136, 129 (1865).
Through an unfortunate oversight during the process of publication, there was omitted from the text of this Communication to the Editor the diagram mentioned therein and shown herewith.-The Editor.
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