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27.5.1.1.1 Variation 1: By Using Hydrogen Sulfide and Acid

DOI: 10.1055/sos-SD-027-00185

Collier, S. J.Science of Synthesis, (200427180.

Early syntheses of thioaldehydes, first pursued in the nineteenth century, involved the treatment of aldehydes with hydrogen sulfide under acidic conditions. Detailed reviews of this early work have been published, and include observations on the preparation of thioformaldehyde and thioacetaldehyde by using this technique.[‌1‌,‌3‌] The unstable thioaldehydes thus produced are often obtained as cyclic trimers or as polymers[‌37‌‌39‌] and, in some cases, yields of the trimers are very high. The use of basic media promotes polymerization and disproportionation of arylthioaldehydes to form benzyl thiols and dithiobenzoic acids by the Cannizarro reaction.[‌37‌]

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