35005-74-4Relevant academic research and scientific papers
2,3;6,7-BIS(2',3'-QUINOLINO)TCU: A RIGID SYN-ORTHOCYCLOPHANE
Thummel, Randolph P.,Lim, Jean-Luc
, p. 3319 - 3322 (1987)
A bis 2,3-quinoline fused derivative of tetracycloundecane is prepared by two sequential Friedlander condensations.An X-ray crystal structure indicates a dihedral angle of 50.5 deg between the two quinoline rings.
Strained heterocyclic systems. Part 21. The Menschutkin reaction
Markgraf,Sangani,Manalansan,Snyder,Thummel
, p. 561 - 563 (2007/10/03)
Rate constants are determined for methyl iodide quaternisations of a series of 2-substituted quinolines and pyridines. Relative rates are interpreted in terms of steric effects, electronic effects and calculated geometries.
Heteroaromatic Fused Derivatives of Tetracyclo4,11.05,9>undecane
Lim, Jean-Luc,Chirayil, Sara,Thummel, Randolph P.
, p. 1492 - 1500 (2007/10/02)
A series of rigid syn-orthocyclophanes is prepared by the Friedlaender condensation of appropriate o-aminobenzaldehyde derivatives with tetracyclo4,11.05,9>undecane-2,7-dione.The reaction may proceed in a stepwise fashion so that unsymmetrical layered compounds can be prepared.These species can be further elaborated by oxidation to quinolinequinones or N-oxides and quaternization to quinolinium salts.Molecular mechanics calculations agree closely with X-ray analysis in describing the structural properties of these cyclophanes.Analysis of the 1H-NMR and UV spectra as well as the reduction potentials of these molecules support a moderate electronic interaction between the decks.Initial investigations regarding their ability to serve as cleft-type hosts are described.
