Toward the Synthesis of Tricyclic Octanes

Abstract

I began my research as a continuation of the summer research of Miss Julie Kugel of Northwestern University. She worked under a National Science Foundation grant. She had begun work on synthesizing Tricyclo (2.1.l.0 24) octane (Ia) or Tricyclo (2.l.1.0 46 ) octane (Ib) or Tricyclo ( 2 . 2 .0 15 .O 45) octane (Ic) or a mixture of all. . . . After she had separated the products by distillation, she followed the above reaction with the addition of bromine by using NBS to the number two carbon and followed this by hydration with a water and acetone mixture to form Bicyclo (3.2.1) -2- octene-4-ol (VI). She then attempted to catalytically hydrogenate the double bond to obtain Bicyclo (3.2.1) octane-4-ol (VII). She was going to follow by oxidizing this reaction with chromic acid to forrn the desired octane (II) (1). It was at this point I began my research. [From Introduction]