Abstract
Sulfidation of Selected Carboxylic and Carbonic Acid Amides with the (9-BBN)2S-Reagent The sulfidation of eight carboxylic and carbonic acid amides (A–H) with bis(1,5-cyclooctanediylboryl) sulfide (1) is described. From the aliphatic acyclic amide A and the N-substituted lactams C–E the corresponding thiocarbonyl compounds 2a and 2c–e, resp., are obtained in high yields. N,N-Dimethylbenzamide (B) reacts with 1 to give monothiobenzoic acid 9-BBN ester (3) and further dithiobenzoic acid 9-BBN ester (4). From N-methylphthalimide (F) and 1 the dithio derivative 5f is formed at room temperature. The carbonic acid amides (urea derivative G, caffeine H) are sulfidated slower than the carboxylic acid amides with formation of the monothio derivatives 2g and 2h, resp. H reacts regioselectively with 1 to yield 6-thiocaffeine (2h) and further to give 2,6-dithiocaffeine (5h).
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