Degree Name
Master of Science (MS)
Semester of Degree Completion
1989
Thesis Director
T. Howard Black
Abstract
Exposure of spiro β-lactones and 3-substituted 4,4-dialkyl oxetan-2-ones to magnesium bromide in diethyl ether solvent resulted in the smooth generation of β,γ-unsaturated acid derivatives in high yield and isomeric purity. It is believed that this reaction occurs via the formation of a stable tertiary carbocation at the β-carbon resulting from cleavage of the carbon-oxygen sigma bond due to the complexation of magnesium cation with the ring oxygen atom. Rapid loss of an adjacent proton then furnishes the unsaturated acids. The β-lactone precursors were prepared by the dehydration of β-hydroxy acid derivatives (obtained from the condensation of ketones with acetic acid dianions) employing benzenesulfonyl chloride in pyridine solvent. Since this synthetic method offers ready access to a wide range of β,γ-unsaturated acids which were previously difficult to obtain, a detailed synthetic methodology and suggestions pertaining to the reaction mechanism are of prime interest and are discussed in detail.
Recommended Citation
Maluleka, Stephen Lucas, "A Novel Synthesis of Cyclic and Acyclic 3-Alkenoic Acids via Ionization/Elimination of β-Lactones" (1989). Masters Theses. 2346.
https://thekeep.eiu.edu/theses/2346
