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

Org Lett. 2022 Jul 29;24(29):5266-5270. doi: 10.1021/acs.orglett.2c01758. Epub 2022 Jul 18.

Abstract

A safe, five-step synthetic route to yield the reliable chemical actinometer, mesodiphenylhelianthrene (MDH), is reported from a commercially available compound. Full characterization 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones* / chemistry

Substances

  • Anthraquinones
  • 1-aminoanthraquinone