An orthomanganation route to 2-substituted derivatives of N-methyl-1,8-naphthalimide

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dc.contributor.authorNicholson, Brian K.
dc.contributor.authorCrosby, Paul M.
dc.contributor.authorMaunsell, Kieran R.
dc.contributor.authorWyllie, Megan J.
dc.date.accessioned2012-10-03T03:03:56Z
dc.date.available2012-10-03T03:03:56Z
dc.date.copyright2012-10
dc.date.issued2012
dc.description.abstractN-methyl naphthalimide can be readily cyclomanganated at the 2-position, directed by the adjacent amide O atom. Di-cyclomanganation also occurs readily to attach Mn(CO)₄ groups at both 2, 7 positions. An X-ray structure determination of the mono-substituted example confirmed the five-membered metallocyclic ring. Cleavage of the Mn–C bond by HgCl₂ or ICl generates 2-substituted HgCl or I derivatives respectively. Reaction of the mono-cyclomanganated N-methyl naphthalimide with phenylacetylene gives an (η⁵-cyclohexadienyl)Mn(CO)₃ complex where the cyclohexadienyl ring has formed by two PhCCH adding in a formal [2 + 2 + 2] process across the C(1)–C(2) bond of the naphthalimide, breaking the aromaticity of the naphthalene ring as shown by a single crystal structure determination.en_NZ
dc.identifier.citationNicholson, B. K., Crosby, P. M., Maunsell, K. R., & Wyllie, M. J. (2012). An orthomanganation route to 2-substituted derivatives of N-methyl-1,8-naphthalimide. Journal of Organometallic Chemistry, 716, 49-54.en_NZ
dc.identifier.doi10.1016/j.jorganchem.2012.06.035en_NZ
dc.identifier.issn0022-328
dc.identifier.urihttps://hdl.handle.net/10289/6675
dc.language.isoen
dc.publisherElsevieren_NZ
dc.relation.isPartOfJournal of Organometallic Chemistryen_NZ
dc.relation.ispartofJournal of Organometallic Chemistry
dc.subjectNaphthalimideen_NZ
dc.subjectCyclometalationen_NZ
dc.subjectManganese carbonylen_NZ
dc.subjectX-ray crystal structureen_NZ
dc.subjectAlkyneen_NZ
dc.titleAn orthomanganation route to 2-substituted derivatives of N-methyl-1,8-naphthalimideen_NZ
dc.typeJournal Articleen_NZ
pubs.begin-page49en_NZ
pubs.elements-id38060
pubs.end-page54en_NZ
pubs.volume716en_NZ
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