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1,3-Dipolare Cycloadditionen von 2-(Benzonitrilio)-2-propanid mit 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thion und Schwefelkohlenstoff

✍ Scribed by Daniel Obrecht; Roland Prewo; Jost H. Bieri; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
660 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

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)‐ad‐ducts 8, 12 and 13 (Schemes 3 and 6). The formation of 8 and 12 can be explained by 1,3‐dipolar cycloaddition of 2‐(benzonitrilio)‐2‐propanide (1b) to the C, S‐double bond of 7. Photochemical isomerization of 12 leads to the third isomer 13 (Schemes 3 and 7). Photolysis of the azirine 11 in the presence of carbon disulfide gives a mixture of two (2:l)‐adducts, namely 12 and 13(Scheme 4). A reaction mechanism via the intermediate formation of the 3‐thiazolin‐5‐thione b is postulated. The structure of the heterocyclic spiro compound 13 has been established by single‐crystal X‐ray structure determination (cf. Fig. 1 and 2).

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