Alcohols thioacyl halides

Thioacylation of Alcohols and Phenols with Thioacyl Halides... 

Thioacyl halides are not easily accessible. Aliphatic derivatives, in particular, can only be isolated in rare cases. Thioacylations of alcohols are therefore less important as synthetic methods than acylation of thiols with acyl hdides. Nevertheless, a variety of 0-alkyl and 0-aryl arenecarbothioates (2) have been obtained according to equation (4i).6.i4,25,2s... 

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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