85234-94-2

Upstream product

• 1067-52-3 tributyltin methoxide 
• 79311-09-4 essigsaeure-<(E)-1-cyano-3-phenyl-2-propenyl>ester 
• 67-56-1 methanol 
• 20068-10-4 (E)-4-phenyl-3-butenenitrile 
• 122-78-1 phenylacetaldehyde 

Relevant academic research and scientific papers

Electrochemical generation and catalytic use of selenium electrophiles

The generation and use of selenium electrophiles in catalytic, electrochemically driven selenenylation-elimination sequences is described. Georg Thieme Verlag Stuttgart.

Catalytic Conversion of β,γ-Unsaturated Esters, Amides and Nitriles into γ-Alkoxy or γ-Hydroxy α,β-Unsaturated Derivatives induced by Persulfate Anion Oxidation of Diphenyl Diselenide

The reaction of β,γ-unsaturated esters, amides and nitriles with catalytic amounts of diphenyl diselenide and an excess of ammonium persulfate in alcohols or in water affords γ-alkoxy or γ-hydroxy α,β-unsaturated derivatives, respectively, in good yields.

Organotin Nucleophiles. 6. Palladium-Catalyzed Allylic Etherification with Tin Alkoxides

Tin alkoxides, although mildly nucleophilic, were found to be highly reactive nucleophiles toward ?-allyl palladium intermediates.Providing a chemoselective approach to allylic etherification, these organotin reagents substitute allylic acetates in the presence of the other electrophilic functional groups such as primary halides.With respect to the two termini of the allylic system, the regioselectivity of nucleophilic attack by tin alkoxides was found to follow the characteristic behavior of stabilized carbanions and amines, namely, preferred attack at the less sterically hindered position and/or at the position remote from an electron-withdrawing substituent.The stereochemical course of the allylic etherification was examined by using an indicator substrate 22b and following the reaction by 1H NMR.Tin phenoxide was found to substitute 10 times faster than epimerization of either starting material or product in a mildly stereospecific manner, the major product retaining the configuration of the starting material.This method has been applied to protect hydroxyl groups of carbohydrates and for selective glycosidation of allylic aglycons.This approach complements the more common Koenigs-Knorr method, providing the α-stereoisomer as the major product.Dialkyloxydialkyltin reagents were found to be as reactive nucleophiles as the monoalkoxide varieties providing a short and useful synthetic approach for obtaining macrocyclic unsaturated polyethers.

Regioselectivity in Organo-Transition-Metal Chemistry. A New Indicator Substrate for Classification of Nucleophiles

A new model for the characterization of nucleophiles is proposed, based on the regioselectivity of the reaction of a given nucleophile with 3-acetoxy-3-cyano-1-phenylpropene (14) in the presence of Pd(0) catalyst.A general correlation between regioselectivity using this indicator substrate and literature data on stereospecificity of nucleophilic substitution in other model compounds is apparent.