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Amidine Dications as Superelectrophiles

Corr, MJ; Roydhouse, MD; Gibson, KF; Zhou, SZ; Kennedy, AR; 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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