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Reaktionen von 1,2,4-Thiadiazol-3,5-dicarbonitril und Röntgenstrukturanalyse von 3-Cyan-1,2,4-thiadiazol-5-carboximidsäure-methylester

✍ Scribed by Roesky, Herbert W. ;Hofmann, Hartmut ;Keller, Klaus ;Pinkert, Waltraud ;Jones, Peter G. ;Sheldrick, George M.

Publisher
Wiley (John Wiley & Sons)
Year
1984
Tongue
English
Weight
257 KB
Volume
117
Category
Article
ISSN
0009-2940

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✦ Synopsis

Eingegangen am 6. Oktober 1983 Aus 1,2,4-Thiadiazol-3,5-dicarbonitril(1) werden die Imidsaureester 2.4, die Thioamide 3.6 und das Dicarboxarnid 5 erhalten. Dabei wird die unterschiedliche Reaktivitat der beiden Nitrilgruppen von 1 gegenuber nucleophilen Reagenzien ausgenutzt. Zuerst erfolgt der Angriff an der Nitrilgruppe in Nachbarstellung zum Schwefel; dies wird durch die Rontgenstrukturanalyse von 2 bestatigt.

Reactions of 1,2,4-Thiadiazole-3,5-dicarbonitrile and X-ray Crystal Structure Analysis of Methyl 3-Cyano-l,2,4-thiadiazole-5-carboximidate From 1,2,4-thiadiazole-3,5-dicarbonitrile (1) the imidic esters 2, 4, the thioamides 3, 6, and the dicarboxamide 5 are obtained using the different reactivity of both nitrile groups of 1 against nucleophilic reagents. The first attack occurs at the nitrile group adjacent to sulfur, as is shown by X-ray structure analysis of 2. 3 I C N CSKHz 6 R R' C (=& H) OCH3 CONHz CONHz CSKH2 CSNHz C ( =NH) OCH3

📜 SIMILAR VOLUMES

Fluorierungsreaktionen an 3,4-Dichlor-1,
Fluorierungsreaktionen an 3,4-Dichlor-1,2,5-thiadiazol
✍ Geisel, Martin ;Mews, Rüdiger 📂 Article 📅 1982 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 359 KB

From the title compound 1 and KF in sulfolane 3-chloro-4-fluoro-(2) and 3,4-difluoro-I ,2,5-thiadiazole (3) are obtained. In the reaction with oxidizing fluorinating agents, e. g. XeF,, BrF,, or AgF,, 2 is the primary product. Cleavage of the ring system at one of the S = N bonds gives the bifunctio