21953-95-7

Usage

Synthesis Reference(s)

Tetrahedron, 52, p. 1943, 1996 DOI: 10.1016/0040-4020(95)01018-1

Upstream product

• 1885-38-7 cinnamic nitrile 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 4360-47-8 cinnamonitrile 

Downstream Products

• 111198-61-9 4-cyanomethyl-N,N-dimethyl-5-oxo-4-phenylhexanamide 
• 848952-08-9 3-(2-methyl-1,3-dioxolan-2-yl)-3-phenylpropionitrile 

Relevant academic research and scientific papers

Mg-promoted regio- and stereoselective C-acylation of aromatic α,/β-unsaturated carbonyl compounds

(matrix presented) Treatment of aromatic α/β-unsaturated carbonyl compounds with Mg turnings in the presence of acid anhydrides/TMSCI or acyl chlorides in DMF brought about a facile and efficient cross-coupling to give C-acylation products, which are usef

Cascade reaction of propargylic alcohols with hydroxylamine hydrochloride: facile synthesis of α,β-unsaturated oximes and nitriles

We have developed an easy and practical method for the synthesis of α,β-unsaturated oximes and nitriles from readily available propargylic alcohols with hydroxylamine hydrochloride (NH2OH·HCl) under metal-free conditions. By using or not using p-toluenesulfonyl chloride (p-TsCl) as the dehydrating promoter, the desired nitriles or oximes could be obtained, respectively via a three-step one-pot or two-step one-pot process in moderate to excellent yields with good functional group compatibility.

Diastereoselective synthesis and ESR study of 4-phenylDEPMPO spin traps

(Chemical Equation Presented) The cis and trans diastereoisomers of 5-(diethoxyphosphoryl)-5-methyl-4-phenylpyrroline N-oxide (4-PhDEPMPOt 8 and 4-PhDEPMPOc 9) were prepared stereoselectively and used as spin traps for hydroxyl and superoxide radicals. Th

Electroreductive acylation of activated olefins using a reactive metal anode

Electroreductive acylation of 3-aryl substituted α,β-unsaturated esters and nitriles in the presence of aliphatic carboxylic anhydrides using reactive metal anode (Mg, Al, Zn) in an undivided cell afforded the corresponding β-acyl compounds in moderate to good yields. It was found that anionic species formed by electron transfer from a cathode may be stabilized by metal ions freshly formed from an anode and undergo electrophilic attack of carboxylic anhydrides to give the β-acyl products in high yields as compared with the previously reported method using a divided cell.

Electrochemical Acylation and Carboxylation of Some Activated Olefins

The electrochemical acylation and carboxylation of some activated olefins have been investigated.Acenaphthylene yields thus on reductive electrochemical acetylation mainly the Z and E enol acetates of 1-(1,2-dihydro-1-acenaphthylidene)ethanone, whereas carboxylation followed by methylation gives trans-1,2-dimethoxycarbonyl-1,2-dihydroacenaphthene.Ethyl cinnamate can be acylated and carboxylated in the 3-position, whereas benzoylacetone could be carboxylated but not acetylated.Neither carboxylation nor acylation were able to compete with the dimerization of benzylidenemalonitrile.Cyclic voltammetry showed that carboxylation generally was faster than acetylation.