dc.contributor.advisor |
Pottie, Ian R. |
|
dc.creator |
Doue, Alyssa Jane |
|
dc.date.accessioned |
2015-07-23T14:00:35Z |
|
dc.date.available |
2015-07-23T14:00:35Z |
|
dc.date.issued |
2014 |
|
dc.identifier.other |
QD262 D675 2014 |
|
dc.identifier.uri |
http://library2.smu.ca/xmlui/handle/01/26258 |
|
dc.description |
x, 104, [70] leaves : ill. (some col.) ; 29 cm. |
|
dc.description |
Includes abstract and appendices. |
|
dc.description |
Includes bibliographical references (leaves 94-104). |
|
dc.description.abstract |
The Nazarov cyclization is a common synthetic tool in the synthesis of cyclopentenone rings. The reaction is characterized by a divinyl ketone starting reagent that undergoes a 4π-electron electrocyclization after addition of a Lewis/Brønsted acid; forming the cyclopentadienyl cation that undergoes cyclization. An extension of this methodology involves using a divinyl imine starting reagent. This cyclization is less favoured due to the electron donating ability of the nitrogen atom, causing the pentadienyl cation to be relatively stable and unwilling to undergo cyclization. To improve this cyclization, the imine is replaced with the electron withdrawing nitronate functionality. It is hypothesized that by doing so the addition of an acid will form the cyclopentadienyl cation that will readily undergo Nazarov cyclization. The synthesis of an aryl vinyl silyl nitronate was optimized and the compound was tested with a number of different acid catalysts to determine if the nitronate Nazarov cyclization is possible. |
en_CA |
dc.description.provenance |
Submitted by Greg Hilliard (greg.hilliard@smu.ca) on 2015-07-23T14:00:35Z
No. of bitstreams: 1
Doue_Alyssa_MASTERS_2014.pdf: 4240953 bytes, checksum: edccd99cd2ccf390e25ed29b69915235 (MD5) |
en |
dc.description.provenance |
Made available in DSpace on 2015-07-23T14:00:35Z (GMT). No. of bitstreams: 1
Doue_Alyssa_MASTERS_2014.pdf: 4240953 bytes, checksum: edccd99cd2ccf390e25ed29b69915235 (MD5)
Previous issue date: 2014-06-25 |
en |
dc.language.iso |
en |
en_CA |
dc.publisher |
Halifax, N.S. : Saint Mary's University |
|
dc.subject.lcc |
QD262 |
|
dc.subject.lcsh |
Organic cyclic compounds -- Synthesis |
|
dc.subject.lcsh |
Ring formation (Chemistry) |
|
dc.title |
Investigation of the nitronate Nazarov cyclization |
en_CA |
dc.type |
Text |
en_CA |
thesis.degree.name |
Master of Science in Applied Science |
|
thesis.degree.level |
Masters |
|
thesis.degree.discipline |
Chemistry |
|
thesis.degree.grantor |
Saint Mary's University (Halifax, N.S.) |
|