Scholarlink

<p>Photochemical dehydrogenation of the 1,3-cyclohexadiene-type ring of 12,13-dihydro-5<i>H-</i>indolo[3,2<i>-c</i>]acridine (<b>1</b>) by singlet oxygen was observed in <i>n</i>-hexane, acetonitrile and methanol. UV irradiation of <b>1</b> leads exclusively to the formation of 13<i>H</i>-indolo[3,2-c]acridine (<b>2</b>) and hydrogen peroxide, where <b>1</b> can itself act as a singlet oxygen sensitiser. Although this type of photooxidation reaction for <b>1</b> might be expected also to yield addition products, such as endoperoxides or hydroperoxides, the oxygenated species were not detected. Our findings are rationalised by DFT calculations of relative energies and conversion barriers involving various possible photooxidation products.</p> Graphical Abstract <p></p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Light-induced oxidative dehydrogenation of 12,13-dihydro-5H-indolo[3,2-c]acridine

  • 期刊论文

  • 发表日期：

    2026年3月20日

查看全文
  • Barbara Golec,
  • Michał Kijak,
  • Krzysztof Nawara,
  • Arkadiusz Listkowski,
  • Randolph P. Thummel,
  • Jacek Waluk

摘要

Photochemical dehydrogenation of the 1,3-cyclohexadiene-type ring of 12,13-dihydro-5H-indolo[3,2-c]acridine (1) by singlet oxygen was observed in n-hexane, acetonitrile and methanol. UV irradiation of 1 leads exclusively to the formation of 13H-indolo[3,2-c]acridine (2) and hydrogen peroxide, where 1 can itself act as a singlet oxygen sensitiser. Although this type of photooxidation reaction for 1 might be expected also to yield addition products, such as endoperoxides or hydroperoxides, the oxygenated species were not detected. Our findings are rationalised by DFT calculations of relative energies and conversion barriers involving various possible photooxidation products.

Graphical Abstract