Title: Macrocyclic Organic Peroxides: Constructing Medium and Large Cycles with O-O Bonds.
Authors: Barsegyan, Yana A.; Vil', Vera A.; Terent'ev, Alexander O.
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.
Subjects: SMALL molecules; PEROXIDES; OZONOLYSIS; POLYMERS; PEROXIDATION; HYDROPEROXIDES
Publication: Chemistry (2624-8549), 2024, Vol 6, Issue 5, p1246
ISSN: 2624-8549
Publication type: Academic Journal
DOI: 10.3390/chemistry6050072

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

Barsegyan, Yana A.; Vil', Vera A.; Terent'ev, Alexander O.