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Four‐membered cyclic peroxides: Carriers of chemical energy
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-8453-5664
2017 (English)In: Journal of Physical Organic Chemistry, ISSN 0894-3230, E-ISSN 1099-1395, p. 1-18Article in journal (Refereed) Published
Abstract [en]

Four‐membered cyclic peroxides are high‐energy compounds often associated tocold light emission, but whose chemical and biological roles are still matters ofdebate. The often‐dangerous synthesis of 1,2‐dioxetanes, achieved around 50 yearsago, has been mastered over the years to a point where some derivatives are commerciallyavailable. This fact does not imply that 1,2‐dioxetanes can be convenientlyprepared in the gram scale or that the synthesis of analogous 1,2‐dioxetanones andthe elusive 1,2‐dioxetanedione are simple. Important questions on the mechanism ofchemiluminescence and bioluminescence reactions are under experimental and theoreticalscrutiny. The available data have contributed to relate structural and mediumeffects to the quantum efficiency of these compounds to produce excited states.Consequently, such peroxides have been suggested to produce biologically relevantelectronically excited species in vivo in the absence of light. The connection of thishypothesis with melanin‐mediated photodamage in the dark has renewed the interestin such cyclic peroxides. This reviewgives some insight on the synthesis, chemiluminescencemechanism, and biological relevance of 1,2‐dioxetanes, 1,2‐dioxetanones,and 1,2‐dioxetanedione and provides practical protocols for those interested inengaging this field.

Place, publisher, year, edition, pages
2017. p. 1-18
National Category
Organic Chemistry
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URN: urn:nbn:se:kth:diva-215158DOI: 10.1002/poc.3725OAI: oai:DiVA.org:kth-215158DiVA, id: diva2:1146684
Note

QC 20171004

Available from: 2017-10-03 Created: 2017-10-03 Last updated: 2017-10-04Bibliographically approved

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Farahani, Pooria

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