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The Use of 2-Bornanethiol for the Asymmetric Synthesis of Amines

dc.contributor.advisorKoch, Andrew
dc.contributor.authorPeterson, Ana
dc.identifier.citationThe University of Maryland McNair Scholars Undergraduate Research Journal, 2, (2010): 209-243.en_US
dc.description.abstractThe proposal to synthesize a camphor sulfinamide reagent using 2-bornanethiol was initiated. A novel disulfide for the synthesis of the reagent was produced through inexpensive means via three synthetic steps. Readily available (+)-camphor underwent thionation using phosphorous pentasulfide in excess. The resulting thiocamphor was reduced to camphor thiol (or 2-bornanethiol) and oxidized to yield camphor disulfide. Further investigation of the disulfide is necessary for confirmation and characterization. Oxidation followed by reaction of the purified sample of this product with ammonia and lithium amide could give camphor sulfinamide. It was determined that purification at the end of each step would help to give better results and cleaner NMR spectra to analyze. Limitations included difficulty with keeping reactions under dry conditions as well as large amounts of time required to run each reaction. From here, the purified disulfide will be used to synthesize camphor sulfinamide which could then be combined with chiral aldehydes and ketones to yield imines in high selectivity.en_US
dc.subjectCamphor sulfinamideen_US
dc.subjectPurified disulfideen_US
dc.titleThe Use of 2-Bornanethiol for the Asymmetric Synthesis of Aminesen_US
dc.relation.isAvailableAtRonald E. McNair Post-Baccalaureate Degree Program
dc.relation.isAvailableAtDigital Repository at the University of Maryland
dc.relation.isAvailableAtUniversity of Maryland (College Park, Md)

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