1365261-19-3Relevant academic research and scientific papers
A new synthesis of cyanocyclopropanes by the intramolecular alkylation of magnesium carbenoids as the key reaction
Saitoh, Hideki,Satoh, Tsuyoshi
scheme or table, p. 3380 - 3384 (2010/08/22)
Addition reaction of 1-chlorovinyl p-tolyl sulfoxides, derived from ketones and chloromethyl p-tolyl sulfoxide, with cyanomethyllithium gave adducts in quantitative yields. Treatment of the adducts with i-PrMgCl in THF resulted in the formation of cyanocyclopropanes via the intramolecular alkylation of the generated magnesium carbenoids. The intermediate of this reaction was proved to be a cyclopropylmagnesium chloride, and it was found to be reactive with electrophiles to give multi-substituted cyanocyclopropanes. The key reaction, intramolecular alkylation of magnesium carbenoid, is the first example for the reaction of the magnesium carbenoids with nitrile-stabilized carbanions.
