Selective derivatisation of resorcinarene ethers <i>via</i> an ortholithiation approach

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Distal functionalisation of C<inf>4</inf>symmetric tetramethoxyresorcinarene by selective lithiation

© 2018, Springer Science+Business Media B.V., part of Springer Nature. Three novel C4symmetric O-substituted derivatives of tetramethoxyresorcinarene were synthesised and characterised and the selective distal lithiation of these derivatives was investigated. Lithiation of the tetraethoxy derivative, followed by quenching with dimethyldisulfide selectively afforded the distal product in 36% yield after removal of unreacted starting resorcinarene. Lithiation of the MOM derivative produced the five possible lithiated products, with the mono being the major product; the distally substituted derivative being a minor product. The benzyloxyresorcinarene appeared to be unstable under the lithation conditions. These results suggest that the selectivity of the distal lithation reaction is heavily dependent on the O-substituents of the resorcinarene