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dc.contributor.authorPetersson, Maria J
dc.contributor.authorMarchal, Camille
dc.contributor.authorLoughlin, Wendy A
dc.contributor.authorJenkins, Ian D
dc.contributor.authorHealy, Peter C
dc.contributor.authorAlmesaker, Ann
dc.date.accessioned2017-05-03T11:07:36Z
dc.date.available2017-05-03T11:07:36Z
dc.date.issued2007
dc.date.modified2009-01-13T07:12:00Z
dc.identifier.issn0040-4020
dc.identifier.doi10.1016/j.tet.2006.11.090
dc.identifier.urihttp://hdl.handle.net/10072/16963
dc.description.abstractRegioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C1 carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoen_AU
dc.publisherElsevier Ltd.
dc.publisher.placeUnited Kingdom
dc.publisher.urihttp://www.elsevier.com/wps/find/journaldescription.cws_home/942/description#description
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom1395
dc.relation.ispartofpageto1401
dc.relation.ispartofissue6
dc.relation.ispartofjournalTetrahedron
dc.relation.ispartofvolume63
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.titleUnexpected regiospecific reactivity of a substituted phthalic anhydride
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, Griffith Institute for Drug Discovery
gro.rights.copyright© 2007 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
gro.date.issued2007
gro.hasfulltextNo Full Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorHealy, Peter C.
gro.griffith.authorLoughlin, Wendy A.
gro.griffith.authorMarchal, Camille
gro.griffith.authorPetersson, Maria J.
gro.griffith.authorAlmesaker, Ann


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