Thiophthalic anhydrides

More commonly, but incorrectly, named thiophthalic anhydride and sometimes referred to as phthaloyl monosulfide or o-phthalyl sulfide, this compound (104) may be prepared by heating phthalic anhydride with sodium sulfide125 or by heating phthaloyl chloride with potassium hydrogen sulfide,126 hydrogen sulfide,127 or ethanolic sodium disulfide.128 The reaction between phthaloyl chloride and hydrogen sulfide also gives phthalic anhydride and di-o-phthaloyl disulfide.127 Early attempts to prepare 104 have been described by Chakravarti.126 4-Nitrophthalic thioanhydride may be prepared by hydrolysis of 8 (R = N02 X = C1) (Section III, A).22... 

Phthalyl chloride is obtained in almost quantitative yield by passing dry chlorine gas into molten thiophthalic anhydride, C,H (CO),S, at 245° until sulfur monochloride no longer distils. Thioanhydrides are made from the oxygen analogs and sodium sulfide. ... 

Imide Single Tg WAXD, SAXS I was made from 3,4 3 4 -biphenyltett a carboxylic dianhydride and 4,4 -oxydianiline II was made from 4,4 -thiophthalic anhydride and 4,4 oxydianiline Zhang et al. (1993)... 

The decarbonylative addition of (thio)phthalic anhydrides to alkynes for the preparation of valuable (thio)isocoumarins is another application of nickel(O) catalysts for the formation of Ar-C(sp ) bonds (Scheme 22.14) [23a, b]. When the reaction is applied to thiophthalic anhydrides, benzothiophenes or thiochromanones can be prepared selectively in place of thioisocoumarins, depending on the reaction conditions employed [23h]. In related reactions, the nickel-catalyzed... 

Thiophthalic anhydride 15 also reacted with various alkynes in the presence of a nickel catalyst to afford sulfur-containing heterocyclic compounds (Scheme 12.8). The use of Ni(0)/PPr3 catalyst in combination with MAD afforded thioisocoumarin 16... 

Inami T, Baba Y, Kurahashi T, Matsubara S. Nickel-catalyzed cycloadditions of thiophthalic anhydrides with alkynes. Org. Lett. 2011 13 1912-1915. 

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