Methylene-bridge-substituted and -coupled calixarenes form via lithiation of tetramethoxy-p-tert-butylcalix[4]arene (1 ). Chloro species 2  is obtained by reaction of lithiated 1  with CCl4 and yields substitution products 3 �6  upon treatment with iodide, H2O, iPrNH2, and ethanol. Lithiated 1  reacts with chloroiodomethane giving 2-chloromethylcalixarene 7 , which is transformed to 2-methylenecalixarene 8  by reaction with NaH in DMF (150 �C). Lithiated 1  reacts with Br2 or BrCH2CH2Br to afford the 2,2'-coupled dicalixarene 9  which is fully demethylated to octahydroxy dicalixarene 10  and then de-tert-butylated to give dicalixarene 11 .

Synthesis and reactions of 2-chlorocalixarene, 2-methylenecalixarene, and 2,2′-dicalixarene compounds

245th National Meeting (2013)

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