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1,3-Dipolare Cycloadditionen von Nitrilium-Betainen mit 4,4-Dimethyl-2-phenyl-2-thiazolin-5-thion by Thomas Büchel; Roland Prewo; Jost H. Bieri; Heinz Heimgartner is a Chemistry article available to read on EtoBox.

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**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.

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Author

Thomas Büchel; Roland Prewo; Jost H. Bieri; Heinz Heimgartner

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

1984

Language

EN

Field

Chemistry (Physical Sciences)