Degree Name

Master of Science (MS)

Semester of Degree Completion

1975

Thesis Director

David H. Buchanan

Abstract

A study was initiated on the hypothesis, by Ugi and co-workers, that cyclopropyl, cyclobutyl, and cyclopentyl electrophiles might under go nucleophilic substitution reactions with retention of configuration.

The synthesis of benzocyclobutenol and 2-phenylcyclobutyl tosylate is described. The reactions of these tosylates with cobalt(I) "supernucleophiles" gave low yields of products which have not been purified sufficiently for assignment of stereochemistry.

Reaction of cyclopentyl tosylate and phenylethyl tosylate with the "supernucleophiles" cobaloxime(I) and cobalt(salen)(I) is discussed for the advance of future work.

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