55090-29-4Relevant articles and documents
Use of Charge-Charge Repulsion to Enhance π-Electron Delocalization into Anti-Aromatic and Aromatic Systems
Sumita, Akinari,Gasonoo, Makafui,Boblak, Kenneth J.,Ohwada, Tomohiko,Klumpp, Douglas A
, p. 2566 - 2570 (2017)
A series of 9-fluorenyl cations has been studied and it is shown that increasing charge on a heterocyclic substituent group enhances the anti-aromatic character of the carbocation system. Similarly, a series of dibenzosuberenyl cations has been studied and increasing charge on a substituent group is shown to enhance aromatic character in the carbocation system. These studies include the direct observations of dicationic and tricationic species using stable-ion conditions and low temperature NMR. The structures of these ions were further characterized using DFT calculations, confirming that highly charged organic ions may exhibit unusual distributions of π-electrons and delocalization of electrons in 4n or 4n+2 π-systems.
Investigation of the solvent enclathration potentials of 5-phenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol and related seven-membered ring alcohols
Taljaard, Benjamin,Barton, Benita,McCleland, Cedric W.
, p. 44 - 48 (2007/10/03)
Four previously reported tricyclic alcohols containing seven-membered central B-rings, 5-phenyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol, 5-phenyl-5H-dibenzo[a,d]cyclohepten-5-ol, 11-phenyl-6,11-dihydrodibenzo[b,e] oxepin-11-ol and 11-phenyl-6,11-dihydrodibenzo[b,e]thiepin-11-ol have been synthesized and their solvent enclathration (inclusion) properties investigated and compared by using 1H-NMR and differential scanning calorimetry (DSC). The presence of an oxygen or a sulphur atom, respectively, in the B-ring of the latter two compounds had a detrimental effect on the solvent enclathration properties of the host compounds as compared to those containing an ethane or ethylene bridge. This suggests that, although enclathration is highly dependent on the hydrogen bonding ability of the host, rigidity of the structure plays a crucial role in the formation and stability of these complexes.
Ritter Reactions. IX. Transannular Addition of Nitriles to the 5H-Dibenzocycloheptene Ring System
Pich, Kim C.,Bishop, Roger,Craig, Donald C.,Scudder, Marcia L.
, p. 837 - 852 (2007/10/02)
The 5H-dibenzocyclohepten-5-ols (1a-e) undergo sequential intramolecular and conventional Ritter reactions with acetonitrile to afford the cyclohepten-11-yl>acetamides (6a-e).Typical yields for these one-flask conversions are 52-64percent, except for the reaction of (1a) where production of the dimeric substance (4a) is favoured.Alcohol (1a) can provide either type of product in good yield, depending on the conditions employed, when reacted with benzonitrile.The molecular skeleton present in the adducts (6) has been confirmed by determination of the crystal structure of (6c) , a 9.188(3), b 14.632(5), c 16.563(9) Angstroem, α 115.64(9), β 90.92(2), γ 96.29(2) deg, Z 4, R 0.043>.
