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

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Show simple item record Nicholson, Brian K. Crosby, Paul M. Maunsell, Kieran R. Wyllie, Megan J. 2012-10-03T03:03:56Z 2012-10-03T03:03:56Z 2012-10 2012
dc.identifier.citation Nicholson, 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.issn 0022-328
dc.description.abstract N-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.language.iso en
dc.publisher Elsevier en_NZ
dc.relation.ispartof Journal of Organometallic Chemistry
dc.subject Naphthalimide en_NZ
dc.subject Cyclometalation en_NZ
dc.subject Manganese carbonyl en_NZ
dc.subject X-ray crystal structure en_NZ
dc.subject Alkyne en_NZ
dc.title An orthomanganation route to 2-substituted derivatives of N-methyl-1,8-naphthalimide en_NZ
dc.type Journal Article en_NZ
dc.identifier.doi 10.1016/j.jorganchem.2012.06.035 en_NZ
pubs.elements-id 38060

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