Premium
The Chemistry of β‐Hydroxy Hydroperoxides
Author(s) -
Louvel Dan,
De Dios Miguel Thomas,
Duc Vu Nam,
Duguet Nicolas
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100343
Subject(s) - allylic rearrangement , singlet oxygen , chemistry , fragmentation (computing) , organic chemistry , combinatorial chemistry , oxygen , catalysis , computer science , operating system
β‐Hydroxy hydroperoxides (β‐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 β‐hydroxy hydroperoxides are presented, such as the photooxidation of allylic alcohols with singlet oxygen and the ring‐opening of epoxides with H 2 O 2 . The main applications of β‐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 β‐hydroxy hydroperoxides, including their stability, safety and characterization through spectroscopic means.