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Regioselektive 1,3-dipolare Cycloadditionen von Thiocarbonyl-yliden mit 1,3-Thiazol-5(4H)-thionen

✍ Scribed by Grzegorz Mlostoń; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
763 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Regioselective 1,3‐Dipolar Cycloadditions of Thiocarbonyl Ylides with 1,3‐Thiazole‐5(4__H__)‐thiones

The thiocarbonyl ylides 13 and 1,3‐thiazol‐5(4__H__)‐thiones 1 undergo a smooth reaction to yield spirocyclic 1,3‐dithiolanes 14–16 (Schemes 4–6). The 1,3‐dipolar cycloadditions occur in a regioselective manner, but the orientation of the thiobcnzophenone‐S‐methylide (13b) differs from that of the cycloalkane thione‐S‐methylides 13a and 13c. Whereas the 1,3‐cycloadduct with 13b is formed in accordance with frontier‐orbital considerations, the inverse orientation in the reactions with 13a and 13c most likely is the result of steric hindrance in the transition state. The thiocarbonyl ylides have been prepared in situ from the corresponding 2,5‐dihydro‐1,3,4‐thiadiazoles 12. The more stable aliphatic precursors 12a and 12c undergo decomposition at 50°, the unstable 12b at −30°.

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