Intermediates in the formation and thermolysis of peroxides from oxidations with singlet oxygen

  • 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.

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Author:Werner Fudickar, Torsten LinkerORCiDGND
ISSN:0004-9425 (print)
ISSN:1445-0038 (online)
Parent Title (English):Australian journal of chemistry
Place of publication:Clayton
Document Type:Article
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
First Page:320
Last Page:327
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert