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Synthesis of Mesodiphenylhelianthrene from 1-Aminoanthraquinone and the Structural Elucidation of Its Endoperoxide Species after Irradiation


Feng, Sheng-Jan; Schumer, Frank; Vandaele, Eva; Meola, Giuseppe; Kradolfer, Flavia; Luber, Sandra; Spingler, Bernhard (2022). Synthesis of Mesodiphenylhelianthrene from 1-Aminoanthraquinone and the Structural Elucidation of Its Endoperoxide Species after Irradiation. Organic Letters, 24(29):5266-5270.

Abstract

A safe, five-step synthetic route of the reliable chemical actinometer, mesodiphenylhelianthrene (MDH), is reported from a commercially available compound. Full characterisation of the intermediates of the synthetic route and the final product MDH are presented together with four crystal structures of intermediates and MDH. The usage of the actinometer is described and finally, the structure of the endoperoxide species (MDHPO), which is formed after irradiation of MDH, has been elucidated experimentally and theoretically.

Abstract

A safe, five-step synthetic route of the reliable chemical actinometer, mesodiphenylhelianthrene (MDH), is reported from a commercially available compound. Full characterisation of the intermediates of the synthetic route and the final product MDH are presented together with four crystal structures of intermediates and MDH. The usage of the actinometer is described and finally, the structure of the endoperoxide species (MDHPO), which is formed after irradiation of MDH, has been elucidated experimentally and theoretically.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
Language:English
Date:29 July 2022
Deposited On:03 Aug 2022 15:19
Last Modified:13 Nov 2022 13:49
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Closed
Publisher DOI:https://doi.org/10.1021/acs.orglett.2c01758
PubMed ID:35849841
Project Information:
  • : FunderSNSF
  • : Grant ID206021_164018
  • : Project TitleDual X-ray Wavelength Single-Crystal Diffractometer
  • : FunderUniversität Zürich
  • : Grant ID
  • : Project Title