Chemie des Dicyans: Reaktionen von Diiminosuccinonitril (DISN) mit Sulfenylchloriden und Chlortrimethylsilan sowie Cyclisierung zu Trifluormethyl‐substituierten 2 H ‐Imidazolen | Zendy

Sundermeyer Jörg | Zendy; Roesky Herbert W. | Zendy

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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 .

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