91349-22-3

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 515-84-4 Ethyl trichloroacetate 
• 41381-97-9 ethyl 2-chloro-3-oxo-3-phenylpropionate 
• 60951-73-7 α-chloro-4-nitro-cis-cinnamic acid 
• 705-54-4 (Z)-α-chlorocinnamic acid 
• 64-17-5 ethanol 
• 60951-73-7 α-chloro-4-nitro-trans-cinnamic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 705-55-5 (E)-2-chloro-3-phenylacrylic acid 

Relevant academic research and scientific papers

Ir(ppy)3-Catalyzed, Visible-Light-Mediated Reaction of α-Chloro Cinnamates with Enol Acetates: An Apparent Halogen Paradox

The visible-light-mediated activation of vinyl chlorides derived from α-chloro ethyl cinnamates via oxidative quenching of excited photocatalyst fac-Ir(ppy)3 is described. Upon photoelectron transfer and chloride extrusion, the corresponding vinyl radical can be efficiently trapped by enol acetates, giving rise to synthetically useful 1,4-dicarbonyl compounds in good to excellent yields. This transformation is distinguished by mild and environmentally benign reaction conditions and can be performed on a multigram scale, in sharp contrast to contrasting α-bromo ethyl cinnamates, which show low conversion under the various conditions applied.

Chemo- and stereoselectivity of the reaction of aromatic aldehydes with triphenylphosphine and trichloroacetic acid derivatives

Aromatic aldehydes react with triphenylphosphine and ethyl trichloroacetate or trichloroacetonitrile to give the corresponding benzylidene dichlorides or α-chlorocinnamic acid derivatives. The chemo- and regioselectivity of these reactions depend on both the substituent in the aromatic ring and reaction conditions. The product configuration was determined on the basis of the coupling constants 2JCH and 3JCH in the 13C NMR spectra. Pleiades Publishing, Inc., 2006.

A convenient synthesis of olefins via deacylation reaction

A convenient and environmentally-friendly synthetic method of olefins via deacylation reaction is described. The reaction gives olefins by condensation of aldehydes with a variety of 1,3-dicarbonyl compounds in the presence of anhydrous potassium carbonate at room temperature in high yields (70-90%) in one step. The synthetic potential of this strategy can be used as an alternative procedure to the Wittig, Wittig-Horner reactions. The stereochemistry of the resulted olefins was determined by NOE experiment with correct radio frequency and X-ray analysis. The E/Z selectivity of the deacylation reaction depends on the α-substituents of the 1,3-dicarbonyl compounds.

Process for the preparation of α-chloromethylene-triorganylphosphorane derivatives

A process for the preparation of α-chloromethylene-triorganylphosphorane derivatives I (radicals R areC-organic substituents and A stands forCNorCO-B where B is aC-organic orO-organic radical which is inert under chlorination conditions) by chlorination of phosphoranes II with chlorine, wherein the chlorination is carried out in the presence of a mineral base as hydrogen chloride acceptor and the chlorine and base are fed to the reaction mixture concurrently but separately at the rates at which they are consumed. The reaction products I are important intermediates for plant protectants.

Stabilized haloylides: Synthesis and reactivity

This paper describes simple and successful methods for the preparation of stabilized halogenated phosphoylides and discusses their stability, reactivity, and utility in organic synthesis. Preparations of several halogenated compounds including pharmaceutically interesting enol lactones are reported.