Journalartikel

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


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

Jahr der Veröffentlichung: 2000

Seiten: 3357-3362

Zeitschrift: European Journal of Organic Chemistry

Bandnummer: 2000

Heftnummer: 19

ISSN: 1434-193X

Verlag: 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.



Zitierstile

Harvard-Zitierstil: 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-Zitierstil: 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

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