Sensitized photoreduction of selected benzophenones. Mass spectrometry studies of radical cross-coupling reactions.

J Photochem Photobiol B

Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznanskiego 8, 61-614 Poznan, Poland; Center for Advanced Technology, Adam Mickiewicz University, Uniwersytetu Poznanskiego 10, 61-614 Poznan, Poland. Electronic address:

Published: September 2022

AI Article Synopsis

  • The study reexamines the hydrogen atom transfer (HAT) reactions between certain benzophenones and 2-propanol, focusing on the production of stable chemical products.
  • The primary products of these reactions are diphenyl and dimethyl ketyl radicals, which subsequently lead to various stable photoproducts through radical coupling processes.
  • The researchers utilized liquid chromatography and high-resolution mass spectrometry to analyze and identify the structures of these photoproducts, while discussing the unclear mechanisms behind the reactions.

Article Abstract

The hydrogen atom transfer reaction (HAT) between selected benzophenones (benzophenone BP, 3-carboxybenzophenone 3CB, and 4-carboxybenzophenone 4CB) and 2-propanol was reinvestigated focusing on stable product analysis. As expected, the primary species of these HAT's are the respective diphenyl and dimethyl ketyl radicals that eventually undergo several radical coupling reactions leading to stable photoproducts. However, the mechanisms of these free radical reactions remain unclear and open to question. In this report, we focus on the detailed analysis of the stable photoproducts of these reactions using liquid chromatography coupled with high-resolution mass spectrometry (LC-ESI-QTOF-MS/MS). Products of photopinacolization (benzpinacol and two diastereoisomers of 4CB and 3CB dimers) and isomeric radical cross-coupling adducts of respective diphenyl and dimethyl ketyl radicals were separated chromatographically, and their structures were determined by high-resolution MS/MS, and the mechanisms of the reactions are discussed.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jphotobiol.2022.112536DOI Listing

Publication Analysis

Top Keywords

selected benzophenones
8
mass spectrometry
8
radical cross-coupling
8
respective diphenyl
8
diphenyl dimethyl
8
dimethyl ketyl
8
ketyl radicals
8
stable photoproducts
8
reactions
5
sensitized photoreduction
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!