dc.contributor.author | Heaney, Frances | |
dc.contributor.author | Bourke, Sharon | |
dc.contributor.author | Cunningham, Desmond | |
dc.contributor.author | McArdle, Patrick | |
dc.date.accessioned | 2018-08-24T08:25:05Z | |
dc.date.available | 2018-08-24T08:25:05Z | |
dc.date.issued | 1998-01-01 | |
dc.identifier.citation | Heaney, Frances; Bourke, Sharon; Cunningham, Desmond; McArdle, Patrick (1998). Steric control of reactivity: formation of oximes, benzodiazepinone n-oxides and isoxazoloquinolinones. Journal of the Chemical Society, Perkin Transactions 2 (3), 547-559 | |
dc.identifier.issn | 0300-9580,1364-5471 | |
dc.identifier.uri | http://hdl.handle.net/10379/9279 | |
dc.description.abstract | Reaction of the alkenyl carbonyl compounds 1 with hydroxylamine can lead to the formation of the oximes 2, the benzodiazepinone N-oxides 3 or the isoxazoloquinolinones 5. The product(s) of reaction are shown to depend on the electronic nature of the terminal olefinic substituent R-3 and the space filling capacity of the substituents R-1, R-2 and R-4. When the olefinic centre is electron poor (R-3 = CO2Et) ketocarbonyls convert exclusively to bicyclic nitrones 3 whereas aldehydes are more sensitive to subtle changes in skeletal structure and give rise to oximes 2, tricycles 5 or mixtures of both, For aldehyde and ketone substrates when the olefinic centre carries an aryl substituent (R-3 = Ph) the primary product of reaction is the corresponding oxime which on thermal activation converts to the tricyclic isoxazoloquinolinones. | |
dc.publisher | Royal Society of Chemistry (RSC) | |
dc.relation.ispartof | Journal of the Chemical Society, Perkin Transactions 2 | |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Ireland | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/ie/ | |
dc.subject | 1,3-azaprotio cyclotransfer | |
dc.subject | potential 1,3-dipoles | |
dc.subject | zh systems | |
dc.subject | nitrones | |
dc.subject | cycloaddition | |
dc.subject | generation | |
dc.subject | x=y | |
dc.title | Steric control of reactivity: formation of oximes, benzodiazepinone n-oxides and isoxazoloquinolinones | |
dc.type | Article | |
dc.identifier.doi | 10.1039/a707857i | |
dc.local.publishedsource | http://eprints.maynoothuniversity.ie/7971/1/FH-Steric-1998.pdf | |
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