The Ley–Griffith oxidation, which is catalyzed by tetra-n-propylammonium perruthenate (TPAP, nPrN[RuO]), is a popular method for not only controlled oxidation of primary alcohols to aldehydes, but also a host of other synthetically useful transformations. While the fundamental reaction mechanism has recently been elucidated, several key hydrogen-bonding interactions between the reagents were implicated but not investigated. Herein the prevalence of H-bonding between the co-oxidant N-methylmorpholine N-oxide (NMO), the alcohol substrate, water and the perruthenate catalyst is established. These observations help to rationalize the importance of drying the reagents and lead to several practical suggestions.

中文翻译：

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Ley-Griffith 氧化中的氢键相互作用：合成化学家的实际考虑

由四正丙基过钌酸铵 (TPAP, nPrN[RuO]) 催化的 Ley-Griffith 氧化是一种流行的方法，不仅可以控制伯醇氧化为醛，还可以进行许多其他合成有用的转化。虽然最近阐明了基本反应机制，但涉及试剂之间的几个关键氢键相互作用但未进行研究。在此，共氧化剂 N-甲基吗啉 N-氧化物 (NMO)、醇底物、水和高钌酸盐催化剂之间普遍存在氢键。这些观察有助于使干燥试剂的重要性合理化，并提出一些实用的建议。