Nucleophilic aromatic substitutions of unactivated aryl halides by methyl selenide anions. Synthesis and selective dealkylations of aryl alkyl selenides

…, M Tingoli, D Chianelli, M Montanucci

文献索引：Tiecco, Marcello; Testaferri, Lorenzo; Tingoli, Marco; Chianelli, Donatella; Montanucci, Manuela Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4289 - 4296

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被引用次数: 59

摘要

Lithium methyl selenide, easily prepared from powdered gray selenium and MeLi, reacts with unactivated aryl halides, in DMF, to afford the aryl methyl selenides as a result of a nucleophilic aromatic substitution. The aryl methyl selenides are rapidly dealkylated in the reaction medium by MeSeLi to give the aryl selenide anions. Addition of an alkyl halide or of cyanogen iodide gives rise to the formation of aryl alkyl selenides or aryl selenocyanates ...