New Syntheses of Bismuthonium Salts, Bismuthonium Ylides and Bismuthane Imides Using Triarylbismuth(V)-Oxo and -Hydroxo Compounds

Abstract

Triarylbismuth(V)-oxo and -hydroxo compounds react with organoboronic acids and esters in the presence of BF₃·OEt₂ to afford the corresponding bismuthonium salts. They also undergo dehydrative coupling with cyclic 1,3-dicarbonyl compounds, amides and sulfonamides to give stabilized bismuthonium ylides, bismuthane N-acylimides and bismuthane N-sulfonylimides, respectively. All reactions proceed efficiently under mild conditions.

Key words

bismuthane oxides - bismuthonium salts - bismuthonium ylides - bismuthane imides

References

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7

When dried in vacuo for several hours, 2a was dehydrated to give a polymeric triphenylbismuthane oxide as an amorphous powder. See Ref. [6]

11

Matano, Y.; Nomura, H.; Suzuki, H. Inorg. Chem., in press.

12

In this reaction, triarylbismuthane and aniline were obtained in good yields. This result suggested that the initially formed triarylbismuthane N-benzoylimide would thermally decompose to generate the bismuthane and phenyl isocyanate. See Ref. [5g]