A Facile Synthesis of a Spironitrone and a Study of its Cycloaddition and Nucleophilic Addition Reactions

Crimmins, DR; Dimitrov, IV; O'Connor, Patrick; Caprio, VE; Brimble, Margaret

dc.contributor.author	Crimmins, DR	en
dc.contributor.author	Dimitrov, IV	en
dc.contributor.author	O'Connor, Patrick	en
dc.contributor.author	Caprio, VE	en
dc.contributor.author	Brimble, Margaret	en
dc.date.accessioned	2011-09-18T22:37:18Z	en
dc.date.issued	2008	en
dc.identifier.citation	Synthesis 2008(20):3319-3325 2008	en
dc.identifier.issn	0039-7881	en
dc.identifier.uri	http://hdl.handle.net/2292/8009	en
dc.description.abstract	The synthesis of spironitrone 5 via microwave-assisted intramolecular alkylation of bromo oxime 10 is reported. The bromo oxime is prepared by alkylation of methyl cyclohexanecarboxylate with 1,4-dibromobutane followed by conversion of the methyl ester to an oxime. Spironitrone 5 undergoes facile 1,3-dipolar cycloaddition to a range of olefins to form a range of spirocyclic isoxazolidines. Nucleophilic addition of several Grignard reagents to spironitrone 5 provided access to a series of alkyl-substituted spirohydroxylamines.	en
dc.language	EN	en
dc.publisher	Georg Thieme Verlag Stuttgart New York	en
dc.relation.ispartofseries	Synthesis	en
dc.rights	Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0039-7881/	en
dc.rights.uri	https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm	en
dc.subject	1,3-dipolar cycloaddition	en
dc.subject	spironitrones	en
dc.subject	microwave	en
dc.subject	Grignard reagents	en
dc.subject	1,3-DIPOLAR CYCLOADDITIONS	en
dc.subject	CYCLIC NITRONES	en
dc.subject	ACID	en
dc.title	A Facile Synthesis of a Spironitrone and a Study of its Cycloaddition and Nucleophilic Addition Reactions	en
dc.type	Journal Article	en
dc.identifier.doi	10.1055/s-0028-1083151	en
pubs.issue	20	en
pubs.begin-page	3319	en
pubs.volume	2008	en
dc.rights.holder	Copyright: Georg Thieme Verlag Stuttgart New York	en
pubs.end-page	3325	en
dc.rights.accessrights	http://purl.org/eprint/accessRights/RestrictedAccess	en
pubs.subtype	Article	en
pubs.elements-id	84047	en
pubs.org-id	Medical and Health Sciences	en
pubs.org-id	Medical Sciences	en
pubs.org-id	Auckland Cancer Research	en
pubs.org-id	Science	en
pubs.org-id	Chemistry	en
pubs.org-id	Science Research	en
pubs.org-id	Maurice Wilkins Centre (2010-2014)	en
pubs.record-created-at-source-date	2010-09-01	en