28478-25-3Relevant academic research and scientific papers
Improved Titanium Tetrachloride Procedure for Enamine Synthesis.II.Scope of the Reaction
Carlson, Rolf,Nilsson, Asa
, p. 49 - 54 (2007/10/02)
The scope of enamine formation by a procedure where the carbonyl compound is added to a preformed titanium tetrachloride-amine complex was investigated with a series of different types of carbonyl compounds and two secondary amines (morpholine and pyrrolidine).The carbonyl compounds include aldehydes, cyclic ketones and some substituted aryl alkyl ketones.Yields of isolated products were in the range 67-100 percent with the exception of the pyrrolidine enamine from camphor which gave 53 percent of the isolated product.
Enamines β-lithiees. I. Preparations et reactions d'alkylation
Duhamel, Lucette,Poirier, Jean-Marie
, p. 297 - 303 (2007/10/02)
The action of alkyllithium reagents on β-bromoenamines 1-9 quickly yields, in THF, β-lithioenamines through halogen - metal exchange.If metallic lithium is used instead of organolithium compounds, β-lithioenamines are also formed but in this case they are accompanied by small amounts of by-products.The action of alkyllithium reagents R1Li on the β-chloroenamine 10 provides a new source of β-lithioenamines in which nucleophilic insertion of the R1 group takes place. β-Lithioenamines are stable compounds even up to 20 deg C in most cases.With alkyl iodides, β-lithioenamines react vigorously even at low temperature.The reaction is stereospecific with retention of configuration.This reaction generates either β-substituted enamines or, by easy acidic hydrolysis, α-substituted carbonyl compounds.The C-alkylation reaction is observed alone.
