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dc.contributor.authorCamp, David
dc.contributor.authorvon Itzstein, Mark
dc.contributor.authorJenkins, Ian D
dc.date.accessioned2017-06-19T04:47:04Z
dc.date.available2017-06-19T04:47:04Z
dc.date.issued2015
dc.identifier.issn0040-4020
dc.identifier.doi10.1016/j.tet.2015.05.099
dc.identifier.urihttp://hdl.handle.net/10072/69227
dc.description.abstractPrevious DFT calculations employing phosphine (PH3) and dimethyl azodicarboxylate showed that a cyclic O,N-phosphorane was energetically favored relative to betaine formation. In this study strong experimental support for the formation of the phosphorane is described. The question of whether betaine formation occurs via nucleophilic attack of the phosphine on the azodicarboxylate as has been previously assumed, or via a [4 cycloaddition (cheletropic) reaction to give the O,N-phosphorane, followed by ring-opening to give the betaine has not been resolved. An answer to this intriguing question is provided.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherPergamon Press
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom4946
dc.relation.ispartofpageto4948
dc.relation.ispartofjournalTetrahedron
dc.relation.ispartofvolume71
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchPhysical organic chemistry
dc.subject.fieldofresearchBiochemistry and cell biology
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode340505
dc.subject.fieldofresearchcode3101
dc.titleThe mechanism of the first step of the Mitsunobu reaction
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
dcterms.licensehttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.description.versionAccepted Manuscript (AM)
gro.rights.copyright© 2015 Elsevier. Licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (http://creativecommons.org/licenses/by-nc-nd/4.0/) which permits unrestricted, non-commercial use, distribution and reproduction in any medium, providing that the work is properly cited.
gro.hasfulltextFull Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorvon Itzstein, Mark


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