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We have examined a series of 1,3-dihydro-1-isobenzofuranamines that exist in an imine/hemiaminal ring-chain tautomerism. The tautomeric free energies are rationalized in terms of electronic and steric effects. A series of compounds bearing substituents of varying bulk have free energies that correlate well with substituent A values.
Arylisobenzofurans can be generated from hemiaminal precursors derived from the reaction of ortho-lithiated benzyl alcohol with 1,3- and 1,4-dicyanobenzene electrophiles. The bis(hemiaminal) products so formed give adducts formally derived from 1,4- and 1,3-phenylenebis(isobenzofuran). The adducts are easily aromatized to functionalized teraryl products.
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