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1,3-Dipolare Cycloadditionen von Nitrilium-Betainen mit 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thion

✍ Scribed by Thomas Büchel; Roland Prewo; Jost H. Bieri; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
937 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

1,3‐Dipolar cycloadditions of Nitrilium Betaines with 4,4‐Dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thione

Benzonitrile ylides, imines, and oxides undergo smooth 1,3‐dipolar cycloaddition reactions with the exocyclic, C,S‐double bond of 4,4‐dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thione (1), yielding heterocyclic spiro‐compounds. The structure of the cycloadducts 5c, 5c′, and 3f (Fig.) have been established by x‐ray structure analysis.

With the benzonitrile ylides, the two regioisomeric cycloaddition modes have been observed, depending on the substituents of the ylide‐C‐atom. It is questionable, whether the reaction of 1 and the oxazaphosphol 8 (Schemes 8 and 13) proceeds via the corresponding nitrile ylide as an intermediate.

📜 SIMILAR VOLUMES

1,3-Dipolare Cycloadditionen von 2-(Benz
1,3-Dipolare Cycloadditionen von 2-(Benzonitrilio)-2-propanid mit 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thion und Schwefelkohlenstoff
✍ Daniel Obrecht; Roland Prewo; Jost H. Bieri; Heinz Heimgartner 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 660 KB

**1,3‐Dipolar Cycloadditions of 2‐(Benzonitrilio)‐2‐propanide with 4,4‐Dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thione and Carbon Disulfide** Irradiation of 2,2‐dimethyl‐3‐phenyl‐2__H__‐azirine (**11**) in the presence of 4,4‐dimethyl‐2‐phenyl‐2‐thiazolin‐5‐thione (**7**) yields a mixture of the three (1:1)