Mechanistic Studies of Alkylation of Cobalt(I) by Cyclopropyl Derivatives

Author

Lailing Magdalene Soong, Eastern Illinois University

Degree Name

Master of Science (MS)

Semester of Degree Completion

1975

Thesis Director

David H. Buchanan

Abstract

A second order nucleophilic substitution reaction with retention of configuration is predicted by Ugi and co-workers if electrophiles such as cyclopropyl, cyclobutyl, or cyclopentyl derivatives undergo substitution under conditions where the S_N2 process is faster than the competing S_N1 process.

A synthesis of both cis and trans-7-chlorobicyclo [4.1.0] heptane from olefin and dichlorocarbene is described. The compound, bicyclo [4.1.0] heptylpyridine [bis(salicylaldehyde)ethylenediiminato] cobalt(III), which contains an alkylcobalt σ-bond, is obtained from the reaction of pyridine [bis(salicylaldehyde)ethylenediiminato] cobalt(I) and 7-chlorobicyclo [4.1.0] heptane. The great light sensitivity of this compound has prevented its isolation in purity sufficient for nmr analysis of stereochemistry.

Observations of thin layer chromatography and several purifications of alkylcobalt(III) compounds are described along with suggestions for further work.

Recommended Citation

Soong, Lailing Magdalene, "Mechanistic Studies of Alkylation of Cobalt(I) by Cyclopropyl Derivatives" (1975). Masters Theses. 3499.
https://thekeep.eiu.edu/theses/3499