Phthalide, 3,3-Diphenyl

Anilino-lluoren-carbong4ure-(9) 14 II 328. N-Xanthyl-benzamid 18 I 557. 7.Anilino-2-metbyl-xanthon 18 II406. 4(oder 7)-Ammo-3.3-diphenyl-phthalid 18 II468. 

The model compounds used to explore the chemistry of imidines can be divided into two basic groups, the diphenylphthalides and the benzylidene phthalides. The first reported synthesis of 3,3-diphenyl-phthalide [1] was by Friedel and Crafts in 1877. Their method involved reacting phthaloyl chloride with benzene in the presence of aluminum chloride. 

Thus the phthaleins are triphenylmethane derivatives, being all derived from phthalophenone (diphenyl phthalide). 

The other group of model compounds are phthalides substituted with a benzylidene group. As with the diphenylated phthalides, the chemistry of these models dates back to the nineteenth century, but the use of this chemistry to give polymers has been achieved primarily by Imai, Ueda and Takahashi, The model for this type of polyimidine was reported by Gabriel in 1885. Phthalic anhydride was reacted with phenylacetic acid in the presence of sodium acetate to give 3-benzyl-idene phthalide [4]. 

The reaction also proceeds through two steps, but unlike the diphenyl-phthalides, forms a stable intermediate. 

Phenylacetyl chloride and hydrocin-namoyl chloride are reduced at mercury to form both acyl radicals and acyl anions as intermediates [76]. From electrolyses of phenylacetyl chloride, the products include 1,4-diphenyl-2-butene-2,3-diol diphenylac-etate, phenylacetaldehyde, toluene, 1,3-diphenylacetone, and l,4-diphenyl-2,3-butanediol, and analogous species arise from the reduction of hydrocinnamoyl chloride. Reduction of phthaloyl dichloride is a more complicated system [77] the electrolysis products are phthalide, biph-thalyl, and 3-chlorophthalide, but the latter compound undergoes further reduction to give phthalide, biphthalyl, and dihydrobi-phthalide. 

Gelatinizzahti (Gelatinizers). Belgrano (Ref 31, pp 218—19) lists Centralites, phthalides, alkyl-phthalates (such as ethyl butyl), diphenyl-urethane and ethylphenylurethane... 

Fhenyl-3-p-toly. phthalid 17, 393, II418. 6-MethyI-3.3-diphenyl-phtbalid 17, 393. 6-Methyl-3.3-diphenyl-phthaIid 17, 393. 

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