This review covers the application, mechanisms and limitations of simple alkylating agents that can be used for the conversion of carboxylic acids to esters, phenols to aryl ethers, enols to enol ethers and thiols to thioethers. Specific recent examples are provided to show the selectivity (regio or chemo) in these transformations. It is important to have access to these methods when considering alternatives to classical alkylating techniques.

The structures of two derivatives of 2‐hydroxy‐1,4‐naphthoquinone (lawsone) are examined using the density functional theory (DFT) hybrid functional B3LYP. Using the optimized structure of lawsone acetate, the reactivity of acyl transfer is described. Also, the nucleophilicity of the conjugate base of lawsone is predicted using the conceptual descriptors related to softness within the DFT framework. Copyright © 2008 John Wiley & Sons, Ltd.

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