TY  - JOUR
A1  - Bauch, Marcel
A1  - Klaper, Matthias
A1  - Linker, Torsten
T1  - Intermediates in the cleavage of endoperoxides
JF  - Journal of physical organic chemistry
N2  - The decomposition of anthracene endoperoxides has been investigated under various conditions. Thermolyses proceed via radical intermediates and afford anthracenes and rearrangement products, depending on the substitution pattern. Interestingly, not only the O-O but also the C-O bond can be cleaved homolytically. Under basic conditions fragmentations take place, affording anthraquinone, and reactive oxygen species. This mechanism explains the often observed decomposition of endoperoxides during work-up. Finally, an acid-catalyzed cleavage has been observed under release of hydrogen peroxide. The results should be interesting for the mechanistic understanding of peroxide decomposition and the endoperoxides might serve as mild sources of reactive oxygen species for future applications. Copyright (C) 2016 John Wiley & Sons, Ltd.
KW  - peroxides
KW  - radicals
KW  - reaction mechanism
KW  - reactive intermediates
Y1  - 2017
U6  - https://doi.org/10.1002/poc.3607
SN  - 0894-3230
SN  - 1099-1395
VL  - 30
PB  - Wiley
CY  - Hoboken
ER  -