The synthesis and diazotization of some aminophenanthrenes
Singleton, Tommy Clark
Doctor of Philosophy
Diazonium salts were first prepared by Griess in 1858 by the reaction of aromatic amines and nitrous acid. In a series of later publications he reported that phenols and aromatic halides are formed by the decomposition of these diazonium salts. However it was not until 1884 that Sandmeyer discovered the ability of cuprous salts to catalyze the conversion of diazonium salts to aryl chlorides and aryl bromides. Since this time this reaction, which bears his name, has been used in most of the preparative work involving the replacement of the diazonium group by these atoms. From the time of their discovery until the present time these reactions have been the object of the study of many organic chemists. The original purpose of this research project was to offer new evidence for the mechanism of these reactions.