Heaney, Frances and Bourke, Sharon and Cunningham, Desmond and McArdle, Patrick (1998) Steric control of reactivity: formation of oximes, benzodiazepinone N-oxides and isoxazoloquinolinones. Journal of the Chemical Society, Perkin Transactions 2, 1998 (3). pp. 547-560. ISSN 1472-779X

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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 R3 and the space filling capacity of the substituents R1, R2 and R4. When the olefinic centre is electron poor (R3 = 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 (R3 = Ph) the primary product of reaction is the corresponding oxime which on thermal activation converts to the tricyclic isoxazoloquinolinones.

Item Type:	Article
Keywords:	Steric control; reactivity; oximes; benzodiazepinone N-oxides; isoxazoloquinolinones;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	7971
Identification Number:	https://doi.org/10.1039/A707857I
Depositing User:	Dr. Frances Heaney
Date Deposited:	24 Feb 2017 16:30
Journal or Publication Title:	Journal of the Chemical Society, Perkin Transactions 2
Publisher:	Royal Society of Chemistry
Refereed:	Yes
Funders:	Eolas, Mayo County Council
URI:	http://pubs.rsc.org
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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