ISSN:
0170-2041
Keywords:
(9-BBN)2S, reagent
;
Sulfidations, regioselective
;
Thiocarboxamides
;
Urea derivatives
;
Thiocaffeines
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Sulfidation of Selected Carboxylic and Carbonic Acid Amides with the (9-BBN)2S-ReagentThe 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).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201177
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