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- Title
Protonation of Tetraphenyl- and 2,3,4-Triphenylcyclo-pentadienone -- An NMR and X-ray Crystallographic Study.
- Authors
Harrington, Laura E.; Britten, James F.; Casey, Michael; Grealis, John; Ortin, Yannick; Müller‐Bunz, Helge; McGlinchey, Michael J.
- Abstract
The protonation of 2,3,4,5-tetraphenylcyclopentadienone (tetracyclone) yields 6,11-diphenyl-5H-benzo[a]fluoren5-one (17) and 2,3,4,5-tetraphenylcyclopent-2-en-1-one (18)as the major products. This contrasts with the pyrolysis of tetracyclone, which yields 5,6-diphenyl-11H-benzo[a]fluoren-11-one (22), a structural isomer of 17. Mechanisms are presented that rationalize these observations. The protonation of 4-hydroxy-2,3,4-triphenylcyclopent-2-en-1-none, the precursor to 2,3,4-triphenylcyclopentadienone, generates 2-(2'-oxo-3',4',5'-triphenylcyclopent-3'-enyl)-3,4,5-triphenylcyclopenta-2,4-dienone (30), which has been unequivocally characterized by X-ray crystallography. The establishment of the conformation of molecule 30 in the solid state, which correlates with the conformation in solution, provides a rationale for the subsequent formation of the tetrahydro-pentaphenyl-as-indacene-3,4-dione (32) upon further protonation.
- Subjects
PROTON transfer reactions; X-ray crystallography; NUCLEAR magnetic resonance; PYROLYSIS; CHEMICAL precursors
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 22, p3249
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201700019