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Selenium-Containing Heterocycles from Isoselenocyanates: 4-Methylselenazole Derivatives from the Reaction with Malononitrile and Propargyl Chloride

✍ Scribed by Geoffroy L. Sommen; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2008
Tongue
German
Weight
233 KB
Volume
91
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Aryl isoselenocyanates 1 react with malononitrile (6a) and propargyl chloride (8) in DMF in the presence of Et~3~N to give the corresponding 2‐(3‐aryl‐2,3‐dihydro‐4‐methyl‐1,3‐selenazol‐2‐ylidene)malononitriles 12 as major products. The analogous reaction takes place with benzoylacetonitrile (6f) instead of 6a. In some cases, the corresponding noncyclic 2‐[(arylamino)(prop‐2‐ynylselanyl)methylidene]malononitriles 9 were obtained as minor products. The structures of 9e and 11a have been established by X‐ray crystallography.

📜 SIMILAR VOLUMES

Selenium-Containing Heterocycles from Is
Selenium-Containing Heterocycles from Isoselenocyanates: Base-Catalyzed Reaction of Malononitrile with Phenyl Isoselenocyanate and Bromoacetonitrile or α-Halogenated Ketones
✍ Geoffroy L. Sommen; Anthony Linden; Heinz Heimgartner 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 German ⚖ 221 KB

## Abstract The reaction of phenyl isoselenocyanate (**1a**) with malononitrile (=propanedinitrile) in DMF in the presence of Et~3~N leads to the intermediate ketene N,Se‐hemiacetal **6a**, which can be trapped with bromoacetonitrile or __α__‐halogenated ketones **12a** and **12b** (__Scheme 3__).