Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Aryltrimethylstannane Cation Radical Fragmentation Selectivities That Depend on Codonor: Evidence for Reactions from Heterodimer Cation Radicals

Aryltrimethylstannane Cation Radical Fragmentation Selectivities That Depend on Codonor: Evidence for Reactions from Heterodimer Cation Radicals
Pu Luo, Joseph P. Dinnocenzo
The aryl/methyl fragmentation selectivities for the photooxidations of phenyltrimethylstannane and (4-methylphenyl)trimethylstannane by 1,2,4,5-tetracyanobenzene in acetonitrile were found to depend on the codonor used to generate the stannane cation radical intermediates. The aryl/methyl fragmentation selectivities for phenyltrimethylstannane and (4-methylphenyl)trimethylstannane varied by factors of 26 and 5.6, respectively, depending on the structures of the codonors. The fragmentation selectivities could be correlated with the oxidation potentials of the codonors and their steric bulk. The results can be interpreted by the intermediacy of heterodimer cation radicals formed between the stannane cation radicals and the neutral codonors, which thereby affect the fragmentation selectivities.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01989

DOI: 10.1021/acs.joc.7b01989

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.