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      Reactions of Some Cyclomanganated Compounds with C-Nitroso Compounds, Allenes, and Ketenimines

      Revell, John Bernard
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      Revell, J. B. (2008). Reactions of Some Cyclomanganated Compounds with C-Nitroso Compounds, Allenes, and Ketenimines (Thesis, Master of Science (MSc)). The University of Waikato, Hamilton, New Zealand. Retrieved from https://hdl.handle.net/10289/2275
      Permanent Research Commons link: https://hdl.handle.net/10289/2275
      Abstract
      eta2-(5-Methoxy-2-acetylphenyl)tetracarbonylmanganese (30) was reacted with 2-methyl-2-nitrosopropane (31) to form 2-acetyl-5-methoxy-N-(tert-butyl)aniline(43) in low yield. Attempts to improve the yield by varying the solvent were unsuccessful.

      Substrate 30 was reacted with nitrosodurene and orthomanganated triphenylphosphine sulfide was reacted with 2-methyl-2-nitrosopropane (31), however no new compounds were characterised in either case.

      Acetylallene (55) was reacted with 30. Electrospray ionisation-mass spectrometry(ESI-MS) provided evidence for the insertion of one and two molecules of 55 into the Mn-C bond of 30 to form the products tentatively identified as 56 and 57.

      The reaction of orthomanganated triphenylphosphine sulfide with acetylallene was attempted but no new compounds were characterised.

      In order to extend the study to ketenimines, the synthesis of the diphenylketene N-(p-tolyl)imine was attempted by the dehydration of N-(p-tolyl)diphenylacetamide under a variety of conditions, but it was not isolated in useful quantities. A single preliminary study of the reaction of diphenylketene N-(p-tolyl)imine with 30 gave an intense green solution, but no products were isolated.
      Date
      2008
      Type
      Thesis
      Degree Name
      Master of Science (MSc)
      Publisher
      The University of Waikato
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