dc.contributor.author |
Browne, Alan Robert |
|
dc.date.accessioned |
2008-08-05T02:19:03Z |
|
dc.date.accessioned |
2022-10-26T20:00:09Z |
|
dc.date.available |
2008-08-05T02:19:03Z |
|
dc.date.available |
2022-10-26T20:00:09Z |
|
dc.date.copyright |
1976 |
|
dc.date.issued |
1976 |
|
dc.identifier.uri |
https://ir.wgtn.ac.nz/handle/123456789/24778 |
|
dc.description.abstract |
The synthesis of the first cyclopropa[b]naphthalene, 1,1-dichloro-2,7-diphenylcyclopropa[b]naphthalene, has been accomplished and the chemistry found to exemplify the strained nature of the three-membered ring. Replacement reactions leading towards other geminally substituted cyclopropa[b]naphthalenes have been investigated and products resulting from intramolecular rearrangement isolated.
Attempts to prepare 1,1-dichlorocyclopropa[b]naphthalene have been investigated but have not been successful.
The synthesis of the parent cyclopropa[b]naphthalene has been achieved by dehydrochlorination of a dichlorobenzobicyclo[4.1.0]heptene. Examination of the product mixtures has revealed the presence of competing concentration-dependent pathways, invoving base induced removal of either the benzylic or cyclopropyl protons. The analogous synthesis of cyclopropabenzene has been re-investigated and strong evidence obtained for similar competing pathways.
Potential routes to cyclopropa[a]naphthalene have been proposed and considerable progress made towards the synthesis of this species. |
en_NZ |
dc.language |
en_NZ |
|
dc.language.iso |
en_NZ |
|
dc.publisher |
Te Herenga Waka—Victoria University of Wellington |
en_NZ |
dc.subject |
Cyclopropanaphthalene |
en_NZ |
dc.subject |
Cyclopropa[a]naphthalene |
en_NZ |
dc.subject |
Cyclopropa[b]naphthalene |
en_NZ |
dc.subject |
Ring formation (Chemistry) |
en_NZ |
dc.title |
Studies of Strained Small-Ring Compounds - Cyclopropanaphthalenes |
en_NZ |
dc.type |
Text |
en_NZ |
vuwschema.type.vuw |
Awarded Doctoral Thesis |
en_NZ |
thesis.degree.discipline |
Chemistry |
en_NZ |
thesis.degree.grantor |
Te Herenga Waka—Victoria University of Wellington |
en_NZ |
thesis.degree.level |
Doctoral |
en_NZ |
thesis.degree.name |
Doctor of Philosophy |
en_NZ |