Date of Award
Master of Science (MS)
David H. Buchanan
A study was initiated on the hypothesis, by Ugi and co-workers, that cyclopropyl, cyclobutyl, and cyclopentyl electrophiles might undergo nucleophilic substitution reactions with retention of configuration.
A simple, high yield synthesis of both cis and trans-2-phenylcyclopropyl chlorides from styrene and chloroform is described. Reaction of each of these alkylating agents with the very nucleophilic cobaloxime super-nucleophile ultimately gave peroxy compounds which appear to arise from insertion of oxygen into the carbon-cobalt bond.
Neither trans-2-phenylcyclopentyl tosylate nor trans-2-phenylcyclohexyl tosylate would alkylate low valent cobaloximes under standard conditions.
A partial synthesis of the 2-phenylcyclobutyl tosylate is described along with suggestions for future work.
Ku, Audrey Yeh, "Mechanistic Studies of Cobalt Super Nucleophiles" (1973). Masters Theses. 3725.
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.