Fumaroyl dichloride

Further reaction of the bromide 33 with acrylonitrile in the presence of PI13P affords the disubstituted product 34 [21]. Selection of amines used in the reaction is critical. Fumaroyl dichloride (35) undergoes oxidative addition, decarbonylation and insertion of acrylate to produce octatrienedioate (36) [22]. 

Fumaroyl chloride 1115 Maleic anhydride (98 g), ca. 94% phthaloyl chloride (230 g), and anhydrous ZnCl2 (2 g) are placed in a flask fitted with a thermometer reaching almost to the bottom and with a 30-cm column which has a heating mantle and is attached to a descending condenser. The mixture is heated for 2 h in an oil-bath so that the internal temperature of the mixture is 130-135° (not higher ) and then allowed to cool to 90-95°, whereafter the crude fumaroyl dichloride is distilled off as fast as possible (b.p. 60-85°/14 mm). Slow fractionation of the distillate gives a 82-95% yield of chloride, b.p. 62-64°/13 mm. This is best stored in a sealed vessel. 

Another extended-chain polyhydrazide which contains no rings was prepared from oxalic di-hydrazide and trans,trans-muconvl dichloride (last formula of Table IV). The polymer had an Tinh value of 0.33 and dissolved in tetramethylammonium hydroxide to form only isotropic solutions. With a higher molecular weight sample, optically anisotropic solutions should be attained. Other possible components for this purpose are fumaroyl and acetylenedioyl (Table IV). ... 

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