Nucleophilic Attack of Nitrocyclopropane with Phenol Derivatives

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Nitrocyclopropanes (NCPs), a class of cyclopropanes that contains a three-carbon ring with a nitrogen dioxide substituent, are important building blocks for designing organic molecules. Their reactivity allows them to participate in many reactions that involve ring opening of the NCP. The purpose of this study was to research reactions with NCP and phenol under microwave irradiation. Reactions with NCP and phenol have been completed previously, but the reaction required heating in an oil bath for 12 hours. The microwave was used to aid in speeding up these reactions and accomplished this task in 1 hour. Once it was determined that the reactions could be done faster, the focus was switched to exploring the scope of the reaction. The base, solvent, and equivalents of the reagents were optimized to ensure complete consumption of the NCP. Other reactions involving NCP and substituted phenols demonstrated the scope of the reaction with electron-donating, electron withdrawing, and sterically hindered structures. Currently, we are obtaining yields for the successful reactions in this project.

Abstract ID :
2019-385
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Spelman College
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Spelman College

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