Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, via Mangiagalli 25, I-20133 Milano, Italy.
J Org Chem. 2021 Nov 5;86(21):15712-15716. doi: 10.1021/acs.joc.1c01469. Epub 2021 Oct 13.
Cyclic ketones were quickly and quantitatively converted to 5-, 6-, and 7-membered lactones, very important synthons, by treatment with Oxone, a cheap, stable, and nonpollutant oxidizing reagent, in 1 M NaHPO/NaHPO water solution (pH 7). Under such simple and green conditions, no hydroxyacid was formed, thus making the adoption of more complex and non-eco-friendly procedures previously developed to avoid lactone hydrolysis unnecessary. With some changes, the method was successfully applied also to water-insoluble ketones such as adamantanone, acetophenone, 2-indanone, and the challenging cycloheptanone.
环酮在 1M 的 NaHPO/NaHPO 水溶液（pH=7）中，用 Oxone（一种廉价、稳定且无污染的氧化试剂）处理，迅速且定量地转化为 5、6 和 7 元内酯，这是非常重要的合成子。在如此简单和绿色的条件下，没有形成羟基酸，因此，以前为避免内酯水解而采用的更复杂且不环保的方法就不再需要了。通过一些改变，该方法也成功应用于一些不溶于水的酮，如金刚烷酮、苯乙酮、2-茚酮和具有挑战性的环庚酮。
