Chart 2 details primary alcohol to aldehyde oxidation examples and an attempted amine to imine reaction. Examples 14-20 detail the effects of substitution on the benzyl ring at the orthometa-para positions including mildly electron donating and withdrawing effects. With the exception of the bisalcohol modest to good conversions to the aldehyde was found. It should be noted that in these cases a large disparity between the percentage conversion to the diagnostic aldehyde 1 H NMR spectral signal (9-11 ppm) and the isolated yield was found in all cases, returning at best a 31% isolated yield .The low boiling point of the aldehyde led to some losses in isolation (and solvent contamination of the final products), combined with the highly reactive nature of the aldehyde product leading to product degradation. Methods to improve isolation included the use of the sodium bisulfite isolation method and preparative TLC over extensive column chromatography. Intriguingly in certain cases the sulfate was formed in preference to the oxidation reaction by comparison to known standards a . Examples that varied the R 1 group including a successful naphthyl derivative , and an unsuccessful fluorenyl example . The reaction was partially successful with a primary aliphatic alcohol but the 1 H NMR spectrum indicated a trace of unreacted starting material (supporting information). An example of oxidising a benzylamine to the imine (24) was attempted but similar to certain primary alcohols led to sulfamation b via comparison to known standards. Taken together, these findings demonstrate both the scope (Chart 1) and limitations (Figure ) of the TESAB method. Based on the revised structure of TESAB we propose the following mechanism (Scheme 1). Scheme 1. Proposed mechanism for how TESAB mediates an all-in-one sulfation and deprotonation to form selectively oxidised products.