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Chemie des Dicyans: Reaktionen von Diiminosuccinonitril (DISN) mit Sulfenylchloriden und Chlortrimethylsilan sowie Cyclisierung zu Trifluormethyl‐substituierten 2 H ‐Imidazolen
Author(s) -
Sundermeyer Jörg,
Roesky Herbert W.
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240706
Subject(s) - chemistry , trifluoroacetic anhydride , pyridine , medicinal chemistry , trifluoromethyl , yield (engineering) , derivative (finance) , stereochemistry , organic chemistry , alkyl , materials science , economics , financial economics , metallurgy
Chemistry of Cyanogen: Reactions of Diiminosuccinonitrile (DISN) with Sulfenyl Chlorides, Chlorotrimethylsilane and Ring Closure to Trifluoromethyl‐Substituted 2 H ‐Imidazoles 4,5‐Dicyano‐2‐hydroxy‐2‐(trifluoromethyl)‐2 H ‐imidazole ( 1 ) is easily prepared by treating DISN with trifluoroacetic anhydride. In the presence of 4‐(dimethylamino)pyridine, however, the O ‐acylated derivative 2 is formed in excellent yield, while the reaction of 1 with chlorotrimethylsilane affords the O ‐silylated product 6 . A bi‐1,2,5‐thiadiazole of the formula S 2 (CN) 4 Cl 2 ( 5 ) is the final reaction product, when DISN is treated with sulfur dichloride in the presence of “naked” chloride ions. On the other hand the non‐heterocyclic N ‐sulfenyl derivative 4 has readily been obtained, when DISN is treated with F 3 CSCl instead. Finally a procedure is described to convert DISN into the corresponding N ‐silylated diimine 3 .