Journal article

Hydrocarbon activation with cerium(IV) ammonium nitrate: Free radical versus oxidative pathways


Authors list: Fokin, AA; Peleshanko, SA; Gunchenko, PA; Gusev, DV; Schreiner, PR

Publication year: 2000

Pages: 3357-3362

Journal: European Journal of Organic Chemistry

Volume number: 2000

Issue number: 19

ISSN: 1434-193X

Publisher: Wiley


Abstract: 
The reactivity of propellane C-C bonds towards cerium(IV) ammonium nitrate (CAN) was studied utilizing photochemical initiation in acetonitrile. Synthetic as well as computational (B3LYP/6-311+G** and MP2/6-31G*) data strongly suggest that the activation of the C-C bonds in cyclopropane and cyclobutane derivatives involves NO3 radical attack on the hydrocarbon ring and does not proceed through single electron transfer. The product structures are not consistent with the intermediate formation of propellane radical cations. These propellane systems could be generated independently by oxidation with charged electrophiles, by anodic oxidation, and through photo-oxidation with 1,2,4,5-tetracyanobenzene; the observed chemical behavior of radical cations is clearly different.



Citation Styles

Harvard Citation style: Fokin, A., Peleshanko, S., Gunchenko, P., Gusev, D. and Schreiner, P. (2000) Hydrocarbon activation with cerium(IV) ammonium nitrate: Free radical versus oxidative pathways, European Journal of Organic Chemistry, 2000(19), pp. 3357-3362. https://doi.org/10.1002/1099-0690(200010)2000:19<3357::AID-EJOC3357>3.0.CO;2-R

APA Citation style: Fokin, A., Peleshanko, S., Gunchenko, P., Gusev, D., & Schreiner, P. (2000). Hydrocarbon activation with cerium(IV) ammonium nitrate: Free radical versus oxidative pathways. European Journal of Organic Chemistry. 2000(19), 3357-3362. https://doi.org/10.1002/1099-0690(200010)2000:19<3357::AID-EJOC3357>3.0.CO;2-R

Last updated on 2025-21-05 at 14:59