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

      Nicholson, Brian K.; Crosby, Paul M.; Maunsell, Kieran R.; Wyllie, Megan J.
      DOI
       10.1016/j.jorganchem.2012.06.035
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      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.
      Permanent Research Commons link: https://hdl.handle.net/10289/6675
      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.
      Date
      2012
      Type
      Journal Article
      Publisher
      Elsevier
      Collections
      • Science and Engineering Papers [3122]
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