Diarylmethane Phthalides

In order that diarylmethane phthalides function as color formers, it is necessary to replace the hydrogen atom in the 3-position of the phthalide ring by an electronegative group. Scheme 5 typifies the synthetic route to such phthalides. Once again the key intermediate is the carboxyben — zophenone which, on treatment with acetic anhydride, yields the 3- acetoxyphthalide.40 Treatment with alkylamines,41 anilines,42 or diphenyl — amines43 leads to the formation of the corresponding 3-amino-substituted phthalides. Finally, ethers and thioethers have also been reported,44 being obtained by reaction of the benzophenone first with thionyl chloride followed by an alcohol, phenol, or thiophenol.

Подпись: Scheme 5
All of these phthalides in which the phthalide ring is not substituted by electron-donating groups are yellow to orange color formers, and useful as

Diarylmethane Phthalides

Scheme 6

shading components for the production of black images. However, introduc­tion of a dialkylamino group into the 6-position of the phthalide ring results in bluish-green shades.

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