141819-18-3Relevant academic research and scientific papers
Generation of allyl- and benzyllithiums from the corresponding halides by the aid of lithium-tellurium exchange reactions
Kanda, Takahiro,Kato, Shinzi,Sugino, Takushi,Kambe, Nobuaki,Sonoda, Noboru
, p. 71 - 84 (2007/10/02)
A variety of allyl- and benzyllithiums were prepared by lithium-tellurium exchange reactions of allylic and benzylic tellurides generated in situ from the corresponding halides.The produced organolithiums were trapped successfully with electrophiles such as aldehydes, ketones, and trimethylchlorosilane.Benzyllithiums having an alkyl, alkoxy,fluoro, chloro, or cyano substituent(s) on their aromatic ring were generated efficiently in THF.Benzylic tellurides bearing a bromo or iodo substituent afforded a mixture of products under similar conditions arising from the competing lithium-halogen exchange and/or the displacement of the halogen atom with organolithiums used, but they were converted selectively to benzyllithiums in ether without affecting halogen substituents on the benzene ring.Several allyllithiums including dilithioisobutene were generated from allylic halides in a similar way via allylic tellurides.Wurtz-type coupling was negligible in any reactions examined. Key words: Tellurium; Lithium; Allyl; Benzyl; Halide
A New Preparative Method of Organoalkali and Organoalkaline-Earth Metals Using Metal-Tellurium Exchange Reactions
Kanda, Takahiro,Sugino, Takushi,Kambe, Nobuaki,Sonoda, Noboru
, p. 103 - 106 (2007/10/02)
Diorganyl tellurides (RTeR') undergoes exchange reaction by the treatment with organometallic reagents of alkali and organoalkaline-earth metals (M = Li, Na, K, MgX and CaX) in a fashion that thermodynamically more stable carbanions are formed, which then react with carbonyl compounds to give corresponding addition products in good yields.The scope and limitation of the exchange reactions are also discussed.
