Studies of the Meyer Reaction and the Hydrogenation of Para Hydroxyphenylarsonic Acid

This investigation was proposed to extend the application of the Meyer reaction to the preparation of arsono dicarboxylic acids and their derivatives as amides and esters.It was hoped that this reaction would ultimately provide a means of preparing alicyclic types of arsonic acids by ring closure of the arsono dibasic acids. Since the reaction did not prove useful for such a synthesis, the second part of the investigation was carried out in an effort to obtain the alicyclic types of arsonic acids from benzenoid arsonic acids. In this investigation the direct arsenation of bromomalonamide, bromo- and chloromalonic ester, diethyl chlorosuccinate, bromo- and chlorosuccinic acid, ethyl (β-bromoethyl)-n-butylmalonate and ethyl(β-bromoethyl)-ethylmalonate was attempted by the Meyer reaction, but under the conditions used the alkali arsenites did not condense with the halogenated compounds. Hydrogenation of p-hydroxyphenylarsonic acid, as attempted in this investigation, resulted in cleavage of the arsono group in preference to reduction of the benzene nucleus. Advisor:C. S. Hamilto