The Chemistry of β-Hydroxy Hydroperoxides

beta-Hydroxy hydroperoxides (beta-hydroperoxy alcohols) are interesting chemical platforms, notably for the preparation of 1,2,4-trioxanes, that are key features of numerous bioactive products such as artemisinin. In this review, the main synthetic methods to prepare beta-hydroxy hydroperoxides are presented, such as the photooxidation of allylic alcohols with singlet oxygen and the ring-opening of epoxides with H2O2. The main applications of beta-hydroxy hydroperoxides are also detailed, including their peracetalization to 1,2,4-trioxanes, their use as epoxidating agents and their fragmentation to carbonyl compounds. A final section is dedicated to the general characteristics and practical aspects of beta-hydroxy hydroperoxides, including their stability, safety and characterization through spectroscopic means.

Automated summary

Beta-hydroxy hydroperoxides are versatile chemical platforms for the synthesis of bioactive compounds like 1,2,4-trioxanes. Various synthetic methods are available to prepare them, and they find applications in the synthesis of 1,2,4-trioxanes, as epoxidating agents, and in the fragmentation to carbonyl compounds. These compounds exhibit characteristics such as stability, safety, and can be characterized through spectroscopic means.