| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5269988 | Tetrahedron Letters | 2010 | 5 Pages |
Abstract
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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Hideki Saitoh, Tsuyoshi Satoh,