Syntheses and Reactions of Trimellitic Thioanhydride and Its Derivatives

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  • IMAI Yoshio
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University
  • TAKAHASHI Takeyoshi
    Department of Polymer Chemistry, Faculty of Engineering, Yamagata University

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  • トリメリト酸チオ無水物およびその誘導体の合成と反応
  • トリメリトサン チオ ムスイブツ オヨビ ソノ ユウドウタイ ノ ゴウセイ ト ハンノウ

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Trimellitic thioanhydride (2) was synthesized by the reaction of trimellitic anhydride (1) with sodium sulfide. Treatment of (2) with thionyl chloride gave 4-chloroformylphthalic thioanhydride (3a). The reaction of (3a) with phenol and thiophenol afforded 4- (phenoxycarbonyl) phthalic thioanhydride (3b) and 4- (phenyl-thiocarbonyl) phthalic thioanhydride (3c), respectively. The reaction of (3a) with aniline yielded 4- (N'- phenylcarbamoyl) -N-phenylphthalimide (6) via 4- (N-phenylcarbamoyl) phthalic thioanhydride (4). The reaction of aniline with (3b) gave 4- (phenoxycarbonyl) -N-phenylphthalimide (5b), whereas that with (3c) afforded (6) via 4- (phenylthiocarbonyl) -N-phenylphthalimide (5c). These results suggest that the reactivity of thioanhydride and other carboxyl derivatives toward nucleophiles decreases in the following order : <BR>C=O-Cl>-C=O-S-C=O->-C=O-S-_??_

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