ISSN:
0009-2940
Keywords:
Charge transfer
;
Circular dichroism
;
Helical molecules
;
[2.2]Metacyclophanes
;
Structure-chiroptic relationships
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Nitro- and Allyloxy-Substituted Helical [2.2]Metacyclophanes: Synthesis, Circular Dichroism and Crystal StructuresThe preparations of the title compound 3a, intraannularly nitro-functionalized, of the extraannularly substituted reference compound 3b, and of the sulfone 4 are described. Enantiomeric resolution of these helical phanes was accomplished on (+)-PTrMA and cellulose tris(3,5-dimethylphenyl)carbamate by HPLC. Racemization of the enantiomers of 3b is faster than that of the previously reported extraannularly substituted phanes. The crystal structure of 3a as well as that of the allyl ether 3d show severe distortions of the benzene rings; the CD spectrum of 3a is pointing at an intramolecular charge-transfer complex, an effect that cannot be evaluated from the CD spectrum of 3b.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240719
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