Despite
the fact that the rim and lateral functionalizations of
pillar[n]arenes have been well explored, ortho-functionalization has rarely been realized. In this
work, we report a facile method of introducing a single functionality ortho to the hydroxyl group in A1/A2-dihydroxypillar[5]arene
via a Grignard addition to pillar[4]arene[1]quinone followed by a
dienone–phenol rearrangement. The described ortho-alkylation/arylation method allowed formation of various mono ortho-alkyl/aryl-substituted A1/A2-dihydroxypillar[5]arenes
previously difficult to obtain.
Unidirectional binding between a pillar[4]arene[1]benzoquinoneoxime host and n-alkyl alcoholic guests was realized with the hydroxy heads of the guests in direct contact with the oxime group of the macrocyclic host.
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