Sterically Demanding Ethylenediamines and Polyamines for the Stabilization of Main Group Elements in Low Coordination Numbers

dc.contributor.advisorDenk, Michael
dc.contributor.authorKrause, Michael
dc.date.accessioned2011-11-23T14:11:37Z
dc.date.available2011-11-23T14:11:37Z
dc.date.copyright2011-11
dc.date.created2011-11-07
dc.date.issued2011-11-23
dc.degree.departmentDepartment of Chemistryen_US
dc.degree.grantorUniversity of Guelphen_US
dc.degree.nameMaster of Scienceen_US
dc.degree.programmeChemistryen_US
dc.description.abstractThis thesis explores the reaction of primary amines with 1,2-dibromoethane and 1,3-dibromopropane as a one step synthesis of N,N"-disubstituted ethylenediamines, RNH- CH2CH2-NH-R, N,N"-disubstituted propanediamines, R-NH-CH2CH2CH2-NH-R and N-substituted azetidines RN[(CH2)3]. Unlike earlier approaches in the literature, this method circumvents the use of the highly toxic #-haloamines. The reaction can also be a convenient approach to N,N",N""-trisubstituted diethylenetriamines which form as byproducts in the synthesis of the ethylenediamines and are readily separated by distillation. The respective propylenetriamines were obtained in analogous fashion from 1,3-dibromopropane. The use of N,Nʼ,N”- trisubstituted triamines for the stabilization of low valent main group compounds was exemplified through the synthesis and structural characterization of a phosphenium salt. N,N'-disubstituted ethylenediamines, R-NH-CH2CH2-NH-R" bearing different substituents R are difficult to obtain and require multi-step protocols. This thesis describes their one step synthesis from aziridines and primary amines. The analogous 1,3-propandiamines were obtained from primary amines and azetidines. N-tert-Butylimidazol was obtained through thermolysis of 1,3-di-tertbutylimidazolium chloride and used as precursor for bis carbenes.en_US
dc.identifier.urihttp://hdl.handle.net/10214/3148
dc.language.isoenen_US
dc.publisherUniversity of Guelphen_US
dc.rights.licenseAll items in the Atrium are protected by copyright with all rights reserved unless otherwise indicated.
dc.subjectethylenediaminesen_US
dc.subjectpolyaminesen_US
dc.titleSterically Demanding Ethylenediamines and Polyamines for the Stabilization of Main Group Elements in Low Coordination Numbersen_US
dc.typeThesisen_US

Files

Original bundle
Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
Krause_Michael_201111_MSc.pdf
Size:
4.55 MB
Format:
Adobe Portable Document Format
Description:
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
317 B
Format:
Item-specific license agreed upon to submission
Description: