Deprotonation of tetramethoxycalix[4]arene 1  followed by CCl4 yields 2-chlorocalix[4]arene 3  as the major product.  To purify this, the product will be substituted with an alcohol to prepare a 2-hydroxycalix[4]arene (4  ), which can then be purified via column chromatography. After conversion of the alcohol to a triflate we will attempt substitution with NaN3 and LiCCH�H2NCH2CH2NH2, to yield 2-azidecalix[4]arene 6  and 2-alkynecalix[4]arene 7  .  Alternatively, 4  will be protected, hydroxylated, propylated, and then treated with a nucleophile so as to undergo an SN2 reaction to yield 10  , a novel calixarene with axial substitution at the 2-position.

Synthesis and reactions of 2-chlorocalixarene

243rd National Meeting (2012)

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