MECHANISM OF THE DIAZOAMINOBENZENE CONVERSION: ADDENDUM 111 connection with a paper published by myself in THISJOURNAL [2, 198, (1937)] dealing with the mechanism of the diazoaminobenzene Conversion, and its analogy with the mobility and fission of keto-enol systems, my attention has been directed recently to the following item from a paper by K. H. Meyer [Ber., U B , 2272, (1921)l. Although reference was made to this publication in relation to the general question of the diazoaminobenzene conversion in the author’s original paper, mention of this reported direct combination of benzenediazonium chloride with aniline hydrochloride was unintentionally overlooked. “5 g festes Benzoldiazoniumchlorid wurden in 20 ccm Wasser gelost und mit einer konzentrierten wassrigen Losung von 4 g festem AnilinChlorhydrat versetzt. Es trat sehr schnell die blaustichig rote Farbe des salzsauren Amino-azobenzols auf, die bei Zusatz von 2.5 ccm 70-proz. Xmcisensaure und 5 ccm einer konzentrierten wassrigen Losung von Natrium-formiat rasch vie1 intensiver wurde. Der bald sich Umkrystallisieren aus Ligroin als Amino-azobenzol, Schmp. 125”.” Since nothing is stated regarding the purity of the precipitated material in the above report, the following comments from a paper by Friswell and Green [ J . Chem. SOC.,47, 919, (1885)l also cited in the author’s original paper) should be added. “Diazoaminobenzene is invariably produced first-when sodium nitrite is added to aniline in solution in excess of strong or dilute acetic acid; when sodium nitrite is added to excess aniline hydrochloride or of any mixture of aniline and aniline hydrochloride, no matter how great the mass-although under such conditions a second reaction slowly takes place with the production of the isomeric compound.’’ H. VINCENTKIDD
THE PEROXIDE EFFECT IN THE ADDITION OF REAGENTS TO UNSATURATED COMPOUNDS. XV. CORRECTION :In the last line of Table I11 (p. 293) of the paper of the above title [J.ORG.CHEM.,2,288-302 (1937)l the ent,ryin the column headed “% 1,2ADDITION PRODUCT” should read “0-10” instead of “90-100.” F. R. MAYO 577
