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jo200580m_si_007.cif (31.73 kB)

Calix[4]arenes with Two Different Chemical Modifications at the Bridges

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posted on 2011-05-20, 00:00 authored by Lev Kuno, Silvio E. Biali
Hexabromocalix[4]arene derivatives (3a and 3b) possessing pairs of dibromomethylene and bromomethylene groups located at distal or proximal positions of the calix scaffold were prepared via photochemical bromination of tetramethoxycalix[4]arene. The dibromomethylene groups undergo hydrolysis to afford calix[4]arenes possessing pairs of carbonyl groups and bromomethylene groups located at distal or proximal bridges (4a and 4b, respectively). The bromomethylene groups of 4 undergo reactions with nucleophiles under SN1 conditions to afford a wide array of derivatives possessing two different chemical modifications at the bridges.

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