76106-64-4Relevant academic research and scientific papers
Helical and Planar-chiral Pyridinophanes - A New Synthesis and Structure/Chiroptic Relationships
Przybilla, Klaus Juergen,Voegtle, Fritz
, p. 347 - 356 (2007/10/02)
A new two-step synthesis for the strained helical oxaphanes 1-5 and for a systematic series of novel structural isomeric (2,4)-pyridinophanes (6-10) is presented.The energy barriers for ring inversion of some intermediate phanes and the kinetics of racemization of the phanes are determined.Separation and enrichment of enantiomers is achieved by HPLC on cellulose tris(3,5-dimethylphenyl)carbamate and poly(triphenylmethyl-methacrylate), resp.The circular dichroism curves of the isomers are compared with those of the corresponding protonated pyridinium compounds.The influence of the chromophor orientation on the circular dichroism is discussed. - Keywords: Circular dichroism/ Helical molecules/ Metacyclophanes/ Oxametacyclophane/ Pyridinophanes
Intramolecular Alkylation of Phenols. Part 4. Base-catalysed Cyclisation of Phenolic Enones. Scope and Limitations
Murphy, William S.,Wattanasin, Sompong
, p. 1555 - 1566 (2007/10/02)
The phenolic enones (4), (5), (8), (9), and (13) cyclise readily under acidic conditions.However, neither these nor the thio-substituted phenols (11a), (13a), (14a), and (15a) closed under basic conditions.Involvement of unfavourable equilibria is disproved.Comparison is made with related successful cyclisations of the saturated ketone (38) and aldehyde (39).Preliminary results suggest that strict stereo-electronic requirements are necessary for enone ring closure and that these conditions are not met in base-catalysed 5-Endo- and 6-Endo-Trigonal ring closures of the phenols of general type (2; n=0 and n=1).
