Cyclopropanation Reactions using Rhodium Acetate tolunitrile complexes as Catalysts
Abstract
In nature, Crysthanimum flowers naturally create Pyrethrin, which is a naturally occurring insecticide. The secret of its structure is having a ring called cyclopropane. Making cyclopropane rings in the lab has some challenges in that catalyst has required to make a cyclopropane ring. As metal catalyst, Rhodium Acetate has been used since 1976. Based on the structure of Rhodium Acetate bis-tolunitrile, one compound has a methyl group in the meta position and the other has a methyl in the para position. The hypothesis is that the meta-tolunitrile complex would facilitate the synthesis of cis cyclopropane over trans cyclopropane. Two isomers of Rhodium acetate tolunitrile were synthesized by reacting alcoholic solution of Meta-tolunitrile or Para-tolunitrile. The resulting product crystallized out of solution. These compounds were used as catalysts for cyclopropantion reactions using ethyldiazoacetate and styrene. The products were analyzed using GC-MS. We discovered that metatolunitrile and the paratolunitrile adducts gave the same trans and cis percentages of cyclopropanes. Further, a blank, not using a dirhodium complex, gave the same percentages of trans and cis cyclopropanes.
Start Time
15-4-2026 9:00 AM
End Time
16-4-2026 10:00 AM
Room Number
219
Presentation Type
Oral Presentation
Presentation Subtype
UG Orals
Presentation Category
Science, Technology, and Engineering
Student Type
Undergraduate
Faculty Mentor
Sandy Eagle
Cyclopropanation Reactions using Rhodium Acetate tolunitrile complexes as Catalysts
219
In nature, Crysthanimum flowers naturally create Pyrethrin, which is a naturally occurring insecticide. The secret of its structure is having a ring called cyclopropane. Making cyclopropane rings in the lab has some challenges in that catalyst has required to make a cyclopropane ring. As metal catalyst, Rhodium Acetate has been used since 1976. Based on the structure of Rhodium Acetate bis-tolunitrile, one compound has a methyl group in the meta position and the other has a methyl in the para position. The hypothesis is that the meta-tolunitrile complex would facilitate the synthesis of cis cyclopropane over trans cyclopropane. Two isomers of Rhodium acetate tolunitrile were synthesized by reacting alcoholic solution of Meta-tolunitrile or Para-tolunitrile. The resulting product crystallized out of solution. These compounds were used as catalysts for cyclopropantion reactions using ethyldiazoacetate and styrene. The products were analyzed using GC-MS. We discovered that metatolunitrile and the paratolunitrile adducts gave the same trans and cis percentages of cyclopropanes. Further, a blank, not using a dirhodium complex, gave the same percentages of trans and cis cyclopropanes.
