TY  - JOUR
A1  - Fudickar, Werner
A1  - Linker, Torsten
T1  - Intermediates in the formation and thermolysis of peroxides from oxidations with singlet oxygen
T2  - Australian journal of chemistry
N2  - Herein we describe the recent mechanistic understandings of the singlet oxygen ene reaction to give hydroperoxides and the [4+2] cycloaddition affording endoperoxides. Both experimental findings and theoretical work conclude in the formation of intermediates structurally similar to perepoxides during the ene reaction. Such intermediates mainly control the regio- and stereoselectivities of this reaction class. For the [4+2] cycloaddition, both a synchronous concerted reaction (benzene, naphthalenes) and a stepwise reaction with a non-symmetric zwitterionic intermediate (larger acenes) have been found. The thermolysis of endoperoxides derived from acenes proceeds stepwise for anthracenes, but in a concerted manner for less stable adducts such as naphthalene.
Y1  - 2014
UR  - https://publishup.uni-potsdam.de/frontdoor/index/index/docId/38311
SN  - 0004-9425
SN  - 1445-0038
VL  - 67
IS  - 3
SP  - 320
EP  - 327
PB  - CSIRO
CY  - Clayton
ER  -