Corr, MJ and Roydhouse, MD and Gibson, KF and Zhou, SZ and Kennedy, AR and Murphy, JA (2009) Amidine Dications as Superelectrophiles. J AM CHEM SOC , 131 (49) 17980 - 17985. 10.1021/ja908191k.
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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.
| Type: | Article |
|---|---|
| Title: | Amidine Dications as Superelectrophiles |
| DOI: | 10.1021/ja908191k |
| Keywords: | SUPER-ELECTRON-DONOR, FREE-RADICAL SUBSTITUTION, CLUSTER-FREE HYDROGENASE, ACTIVE-SITE MODELS, DIQUATERNARY SALTS, CRYSTAL-STRUCTURE, TRIPLE RESONANCE, TERTIARY AMIDES, METHANOGENIC ARCHAEA, PYRIDINE-DERIVATIVES |
| UCL classification: | UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry |
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