The synthesis of ethyleneimines from ?-haloaminoethane

dc.contributor.advisorDenk, M.K.
dc.contributor.authorScotland, Kevin M.
dc.date.accessioned2021-04-19T14:27:15Z
dc.date.available2021-04-19T14:27:15Z
dc.date.copyright2009
dc.degree.departmentDepartment of Chemistry and Biochemistryen_US
dc.degree.grantorUniversity of Guelphen_US
dc.degree.nameMaster of Scienceen_US
dc.description.abstractThis thesis describes a simple method for the synthesis of ethyleneimines. Ethyleneimines have historically found use as cancer drugs as well as starting materials for amines, amides and N-heterocycles. However, there is very little accurate data on some of these compounds most basic characteristics; one such characteristic is the energy of the nitrogen inversion barrier of ethyleneimines. Herein, the inversion barriers were calculated with the CBS-Q method and compared with experimental data obtained from dynamic NMR. The primary aim of this investigation was to develop a large scale method for ethyleneimines on a kilogram scale. To this end we investigated the reaction of primary amines with 1,2-dibromoethanes, in a variety of polar and non polar solvents using different bases. These reactions failed to produce a viable synthetic method. This prompted the development of a high yielding synthesis for the 1-bromo-(2-alkylamino)ethane·hydrobromide, utilizing the amino alcohol, and a 48% hydrobromic acid solution, resulting in yields of ranging from 81-89% for R=Me, Et, 'i'-Pr, ' t'-Bu, Ph.en_US
dc.identifier.urihttps://hdl.handle.net/10214/25050
dc.language.isoen
dc.publisherUniversity of Guelphen_US
dc.rights.licenseAll items in the Atrium are protected by copyright with all rights reserved unless otherwise indicated.
dc.subjectethyleneiminesen_US
dc.subjectbeta-haloaminoethaneen_US
dc.subjectsynthesisen_US
dc.subjectinversion barriersen_US
dc.titleThe synthesis of ethyleneimines from ?-haloaminoethaneen_US
dc.typeThesisen_US

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