Document Type

Article

Publication Date

4-17-2024

Abstract

Nucleophilic additions to epoxides are an important class of reactions in organic chemistry which have found use in material science, as intermediates, and in the synthesis of biologically important compounds. Many nucleophiles add to epoxides via a SN2 mechanism at the least substituted carbon. However, under acidic conditions addition is at the most substituted carbon via a SN1 mechanism. Included within this class of reactions is the addition of carboxylic acids to epoxides using tetrabutylammonium bromide as the catalyst. These reactions are straight forward and give high yields of the product. However, previous work in our lab using phthalimide as the nucleophile showed a faster reaction rate with tetrabutylammonium fluoride. Due to this result, we were interested in studying the effect of halide on the addition of benzoic acid to styrene oxide. To better understand this reaction and the role of the catalyst, the halide of the ammonium salt was varied (F-, Cl-. Br‑, and I‑). Reaction times were determined by IR spectroscopy and the product ratio was determined using proton NMR spectroscopy. The results, reaction times and ratio of products, of these studies will be reported.

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