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Amidine dications as superelectrophiles.

Michael J Corr¹, Mark D Roydhouse, Kirsty F Gibson

¹WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.

Journal of the American Chemical Society

|November 18, 2009

Summary

New N-methyl disalts are powerful methylating agents, outperforming dimethyl sulfate. These compounds react with nucleophiles like nitrogen, phosphorus, and even water, forming pyridones and offering a versatile new tool in methylation chemistry.

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Methylating agents are crucial in organic synthesis.
Dimethyl sulfate is a common but hazardous methylating agent.

Purpose of the Study:

To synthesize and characterize novel N-methyl disalts.
To evaluate their efficacy as methylating agents.
To compare their reactivity against established agents like dimethyl sulfate.

Main Methods:

Synthesis of pyridinium and pyrimidinium ditriflate salts.
Competition experiments with various nucleophiles (phosphorus, nitrogen, oxygen).
Characterization of synthesized compounds and reaction products.

Main Results:

N-methyl disalts exhibit potent methylating activity towards phosphorus and nitrogen nucleophiles.
These disalts demonstrate higher reactivity than dimethyl sulfate in competitive methylation.
Reaction with water yields 2-pyridones via ring attack and ammonium displacement.
A tricationic analogue was synthesized and its methylating potential assessed.

Conclusions:

Novel N-methyl disalts represent highly effective and potentially safer alternatives to dimethyl sulfate.
The reactivity profile allows for selective methylation of diverse nucleophiles.
The demonstrated versatility opens avenues for new synthetic strategies.