Picture of aircraft jet engine

Strathclyde research that powers aerospace engineering...

The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by University of Strathclyde researchers, including by Strathclyde researchers involved in aerospace engineering and from the Advanced Space Concepts Laboratory - but also other internationally significant research from within the Department of Mechanical & Aerospace Engineering. Discover why Strathclyde is powering international aerospace research...

Strathprints also exposes world leading research from the Faculties of Science, Engineering, Humanities & Social Sciences, and from the Strathclyde Business School.

Discover more...

Amidine dications as superelectrophiles

Corr, Michael J and Roydhouse, Mark D and Gibson, Kirsty F and Zhou, Sheng-Ze and Kennedy, Alan R and Murphy, John A (2009) Amidine dications as superelectrophiles. Journal of the American Chemical Society, 131 (49). pp. 17980-17985. ISSN 0002-7863

Full text not available in this repository. (Request a copy from the Strathclyde author)

Abstract

2-Dimethylalkylammonium pyridinium and 2-dimethylalkylammonium pyrimidinium ditriflate salts are very powerful methylating agents toward phosphorus (triphenylphosphine) and nitrogen (triethylamine) nucleophiles. In competition experiments with triethylamine as nucleophile, these N-methyl disalts are more reactive methylating agents than dimethyl sulfate. Reaction of the pyridinium dications with water as an oxygen nucleophile leads to attack at the 2-position of the heteroaromatic ring and displacement of an ammonium group; 2-hydroxypyridinium compounds are formed in the first instance, which are easily converted to 2-pyridones. Extending the scope of the reactions, a tricationic 2,6-bis(dimethylalkylammonium) pyridinium salt has also been prepared and characterized and its reactivity as a methylating agent assessed in comparison with that of the dications.