Abstract

This review deals with the synthesis and preparative uses of metallic derivatives of primary and secondary arsines, stibines, and bismuthines. Reaction of these derivatives (usually called arsenides, stibides, and bismuthides) with organic halides has become an important synthetic pathway to tertiary arsines, stibines, and bismuthines. They have also proved useful for the preparation of organic compounds containing covalent bonds between arsenic or antimony and silicon, germanium, tin, or lead. A number of secondary arsines have been obtained by the reaction of arsenides of the type RAsHNa with alkyl halides. 1. The Cleavage of Triarylarsines or Triarylstibines with Alkali Metals. 2. The Cleavage of Diarsines, Bis[diarylarsenic] Oxides, and Arseno Compounds. 3. The Reaction of Secondary Arsines and Stibines with Organolithium Compounds or with Alkali Metals. 4. The Reaction of Primary Arsines with Sodium or Potassium. 5. The Reaction of Primary Arsines with Organolithium Reagents. 6. Reactions in which Haloarsines, Halostibines, or Halobismuthines react with an Alkali Metal. 7. Reactions of the Alkali Metal Arsenides M3As and (M2As)2 and the Alkali Metal Stibides M3Sb and (M2Sb)2 with Alkyl Halides. 8. Miscellaneous Reactions.

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