Substituted triphenyl tetrazolium chlorides

The work in this thesis is a continuation of a project started at the University of Richmond in 1952 by A. G. Richardson under the directorship of Dr. J. S. Pierce and Dr. George z.Williams, Director of Clinical Pathology, National Institutes of Health, Bethesda, Maryland. The purpose of the research was to prepare triphenyl tetrazolium salts, substituted, particularly in the ortho and para positions, with various electron accepting and electron donating groups. It was hoped that these substitutions would impart enough differences in the properties of the compounds so as to allow d etection of certain biological reactions. The tetrazolium salts were sent to Dr. Williams for testing as soon as they were prepared. Time has not permitted the biological testing of the com­ pounds prepared in this work to be completed. However, a number of the salts, as well as those prepared by Richardson have been tested in Dr. Williams\u27 laboratories. The substitutions which have been used were chosen from a number of groups which varied with respect to their electron donating and electron accepting power. The list as given in Fuson\u27s Advanced Organic Chemistry was used as a guide. The groups listed in order of decreasing nucleophylic power are as follows: -NH2, -OH, -OCH3, + -CH3, -H, -C6H5, - COCH3 , -No2, and -N(CH3)3 (8s). Piperonal, because of availability and electron donating power, was used to give a 3,4-methylenedioxy substitution on the phenyl group in position 5 of the tetrazolium molecule