3 years ago

Light-Induced Reactions of Diazotetrahydrofuranone without Elimination of Nitrogen: Experimental and Mechanistic Study

Light-Induced Reactions of Diazotetrahydrofuranone without Elimination of Nitrogen: Experimental and Mechanistic Study
Olesia S. Galkina, Nina L. Tonogina, Valerij A. Nikolaev, Liudmila L. Rodina, Alexey V. Povolotskiy, Victor I. Baranovskii
The energies and lifetimes of the excited states (S1, S2, S5, T1) of a diazotetrahydrofuranone were determined using experimental and computational methods. It was shown that direction of the diazoketone photochemical transformations without elimination of nitrogen is determined by multiplicity and energy of the excited state, generated by UV irradiation of diazo compound: isomerization to α-ketodiazirine proceeds from the singlet S1 state, whereas the alternative process of C–H insertion with hydrazone formation occurs through the triplet T1 state. The most probable excited state that leads to elimination of nitrogen and Wolff rearrangement is one of the highest singlet excited states of diazotetrahydrofuranone.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01848

DOI: 10.1021/acs.joc.7b01848

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.