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Synthesis of Functionalized Oxacalix[4]arenes.

✍ Scribed by Jeffrey L. Katz; Michael B. Feldman; Rebecca R. Conry


Publisher
John Wiley and Sons
Year
2005
Weight
20 KB
Volume
36
Category
Article
ISSN
0931-7597

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Unprecedented chiral oxacalixarenes were obtained from the reaction of (Β±)-1,1 0 -binaphthyl-2,2 0 -diol (BINOL) with 1,5-difluoro-2,4-dinitrobenzene. Structural elucidation of C 2h -symmetric meso (R,S)-oxacalix[4]arene and D 2 -symmetric racemic (as well as enantiopure) (R,R)-and (S,S)-oxacalix[4]

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Novel azo-calix[4] arenes have been prepared by the incorporation of both ester and amide groups. Six bis(phenylazo)-O-substituted calix[4]arene derivatives were isolated and fully characterized. NMR analyses show that these compounds are in cone conformation in solution at room temperature.