Various synthetic schemes were used to prepare a number of new amino-thio- and sulfonyladamantane compounds. By a nucleophilic substitution on 1-bromoadamantane, 1-(p-nitrophenylthio)adamantane was prepared from p-nitrothiophenol; the amino- and sulfonyl- derivatives of this compound were also prepared. Silver tosylate was used to generate the 1-adamantyl carbonium ion from 1-bromoadamantane in a synthetically useful procedure for preparing 1-adamantylamides from nitriles. Three 1-(1-adamantylcarbinyl)-2,5-dialkylpyrroles were prepared by Knorr-Paal reactions and reduced to the corresponding pyrrolidines. Thio- and aminomethyl 1-adamantyl ketones were prepared from methyl and bromomethyl 1-adamantyl ketones, respectively. Aliphatic and aromatic oxiranes were reacted with 1-aminoadamantane in a bomb at elevated temperatures to give several new 2-(1-adamantylamino)ethanol derivatives.
College and Department
Chemistry and Biochemistry
BYU ScholarsArchive Citation
Argyle, Joseph Craig, "Preparation of new amino-, thio-, and sulfonyladamantane derivatives" (1970). Theses and Dissertations. 8156.
Aminonyladamantane derivatives, Thionyladamantane derivates, Sulfonyladamantane derivatives