Allyl Radical Nature of a Phenylcyclopentadienyl Radical Annelated with Two Homoadamantene Frameworks
- 23 June 2011
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 76 (15), 6095-6100
- https://doi.org/10.1021/jo200748m
Abstract
1-Phenylcyclopentadiene fused with two homoadamantene units at the 2,3- and 4,5-positions (4) was deprotonated with KH to lead to the quantitative formation of the corresponding cyclopentadienyl (Cp) anion 3–. This anion was oxidized by AgCl to afford an orange crystalline solid consisting of Cp radical 3• and cyclopentadiene 4. The ESR spectrum in hexane exhibited approximately 15 lines, demonstrating that the two homoadamantene frameworks were equivalent and that the C1–C2(Ph)–C3 moiety of the five-membered ring formed a symmetrical allyl-like radical in agreement with the prediction by DFT calculation. The reaction of the Cp radical 3• with an oxygen molecule in the presence of Ag+SbF6– afforded the SbF6– salt of a phenylpyrylium ion annelated with two homoadamantene frameworks (8+SbF6–).Keywords
This publication has 30 references indexed in Scilit:
- Pentaisopropylcyclopentadienyl: singlet anion, doublet radical, and triplet cation of a carbocyclic .pi. systemJournal of the American Chemical Society, 1993
- The structure and remarkable stability of a per-pyridinium substituted allyl radicalJournal of the American Chemical Society, 1991
- Pentabenzylcyclopentadienylpotassium ṁ 3 THF, an Organopotassium Compound with “Piano Stool” GeometryAngewandte Chemie-International Edition, 1989
- Alkyl group stabilization of monoolefin radical cations. ESR, ENDOR, and cyclic voltammetry studyJournal of the American Chemical Society, 1981
- Electrochemistry of pyrylium compounds—II[1]. Structural effects on the voltammetric behavior in acetonitrileElectrochimica Acta, 1980
- The photolysis of cyclopentadienyl compounds of tin and mercury. Electron spin resonance spectra and electronic configuration of the cyclopentadienyl, deuteriocyclopentadienyl, and alkylcyclopentadienyl radicalsJournal of the Chemical Society, Perkin Transactions 2, 1980
- Potential surfaces for the planar cyclopentadienyl radical and cationJournal of the American Chemical Society, 1979
- Übergangsmetall-Komplexe, II1) Reaktionen von Nickel(0) mit RadikalenEuropean Journal of Organic Chemistry, 1973
- Study of Molecular Orbital Degeneracy in C5H5The Journal of Chemical Physics, 1965
- Jahn-Teller Distortions in Cyclobutadiene, Cyclopentadienyl Radical, and Benzene Positive and Negative IonsThe Journal of Chemical Physics, 1960