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Chemistry, volume 6, issue 5, pages 1246-1270

Macrocyclic Organic Peroxides: Constructing Medium and Large Cycles with O-O Bonds

Publication typeJournal Article
Publication date2024-10-15
Journal: Chemistry
scimago Q2
wos Q3
SJR0.426
CiteScore3.2
Impact factor2.4
ISSN26248549
Abstract

Macrocycles bridge the gap between conventional small molecules and polymers. Drawing inspiration from successful carbon heteroatom-containing macrocycles, peroxide-containing macrocycles are gaining attention for enhanced bioactivity, potential chelating properties, and applications in energetic materials. This review presents the following strategies for the construction of cyclic peroxides with 10- to 36-membered frameworks: (1) the intramolecular iodocyclization of hydroperoxides, (2) the intermolecular cyclization of hydroperoxides with alkyl dihalides or carbonyls, (3) the acid-catalyzed rearrangements of ozonides or 11-membered cyclic triperoxides via oxy- or peroxycarbenium ions, and (4) the peroxidation of carbonyls targeting macrocyclic peroxides. The specific agents that allow for the selective construction of the medium and large cycles are also analyzed.

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