81040-24-6

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 

Downstream Products

• 92010-47-4 (E)-4-Hydroxy-2-methyl-1-phenyl-pent-1-en-3-one 
• 100573-18-0 2,3-Dimethyl-4-phenyl-2-(trimethylsiloxy)-3-butennitril 
• 647024-78-0 (E)-4-methyl-5-phenylpent-4-ene-2,3-dione 
• 908260-64-0 (E)-5-Ethyl-2-methyl-1-phenyl-hept-1-ene-3,4-dione 
• 908260-61-7 (E)-2,6-Dimethyl-1-phenyl-hept-1-ene-3,4-dione 
• 908260-60-6 (E)-2-Methyl-1-phenyl-hept-1-ene-3,4-dione 
• 908260-63-9 (E)-2,5-Dimethyl-1-phenyl-hex-1-ene-3,4-dione 
• 100573-11-3 C₁₄H₁₈LiNOSi 

Relevant academic research and scientific papers

Lewis base-catalyzed transformation of α,β-unsaturated aldehydes to saturated carboxylic acids, esters and amides

The reactions of α,β-unsaturated aldehydes such as (E)-cinnamaldehyde and 2- or 4-methoxycinnamaldehyde with trimethylsilyl cyanide in the presence of a catalytic amount of a Lewis base such as TTMPP and DBU afforded the corresponding saturated carboxylic acids after hydrolysis.

Trimethylsilyl Cyanide - A Reagent for Umpolung, XI. On the Ambident Character of Substituted Allylic Anions.

The dependence of the α/γ-ratio of alkylation products on several factors has been determined with 1-cyano-3-aryl-1-(trimethylsiloxy)allylic anions.Increasing amounts of γ-product are found in more polar solvents, with larger alkali ions, on addition of HMPT, with smaller alkyl groups in the electrophile, and especially with p-cyanophenyl groups.In contrast, temperature and leaving groups have minor effects.On substitution of the O-silyl group by O-methyl and O-ethoxycarbonyl, α-alkylation predominates strongly.The results are compared to known allylic anions.Furthermore, the isomerisation of compounds of type C to type B is described as well as a new addition reaction of cyanoformates to aldehydes.