Thiocarbonyl compounds thioacylation

R = Ph) is also formed in the reaction between diazomethane and thiobenzoyl chloride, probably via a 1,3-dipolar addition of diazomethane to the thiocarbonyl group. Similar additions have been observed by Huisgen et The reaction between thioacyl chlorides and diazo compounds was first studied by Staudinger and Siegwart.i 3 (R = Ph) has been prepared by cyclization of 11 with triethylortho-formate, and also from 2-phenyl-1,3,4-oxadiazole and phosphorus pentasulfide. ... 

In general, thiocarbonyl halides (59) function as thioacylation reagents with a variety of nucleophiles to yield the appropriate thio derivatives (60) (Scheme 31). For example, (59) on condensation with thiols, amines, potassium cyanide or potassium thiocyanide yields the corresponding thio compounds (60). Thiolocarboxylic acids (50) characteristically acylate alcohols and amines with desulfuration (Scheme 32). Dithiocarboxylic acid esters (54b) react with organolithium or Grignard reagents to give the dithioketals (61) after treatment with an alkyl halide (Scheme 33). 

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