tpap[cite]10.1055%2Fs-1994-25538[/cite], as it is affectionately known, is a ruthenium-based oxidant of primary alcohols to aldehydes discovered by Griffith and Ley. Whereas ruthenium tetroxide (RuO4) is a voracious oxidant[cite]10.1139/v76-304[/cite], its radical anion countered by a tetra-propylammonium cation is considered a more moderate animal[cite]10.1021/jo00038a009[/cite]. In this post, I want to try to use quantum mechanically derived energies as a pathfinder for exploring what might be going on (or a reality-check if you like).