160685-76-7Relevant academic research and scientific papers
Fluoride-ion-mediated reactions of trimethylsilylacetylene with carbonyl compounds and terminal acetylenes
Abele, Edgars,Rubina, Kira,Abele, Ramona,Popelis, Juris,Mazeika, Ilona,Lukevics, Edmunds
, p. 184 - 189 (1999)
Fluoride-ion-mediated reaction of trimethylsilylacetylene with carbonyl compounds has been thoroughly studied. The products of addition to the C=O bond were obtained in 15-66% yield, their subsequent silylation and addition to the second molecule of the c
Trimethylsilylphenylacetylene in C-Alkynylation Reactions
Komissarova,Aleksandrova,Stadnichuk
, p. 412 - 416 (2007/10/03)
Direction and yields of products of the reaction between phenylethynyl anions, generated from trimethylsilylphenylacetylene under the action of potassium fluoride in DMF, and C-electrophilic reagents (aliphatic and aromatic aldehydes and ketones, aliphatic and aromatic acyl chlorides, aryl halides, and alkenyl chlorides with chlorine in the allylic position) are controlled by their structure. Secondary acetylenic alcohols prepared from aromatic aldehydes, as well as their trimethylsilyl ethers, undergo uncatalyzed Meyer-Schuster rearrengement.
FLUORIDE CATALYZED REACTION OF SILYLACETYLENES WITH CARBONYL COMPOUNDS
Kuwajima, I.,Nakamura, E.,Hashimoto, K.
, p. 975 - 982 (2007/10/02)
(Phenylethynyl)trimethylsilane undergoes nucleophilic addition to a variety of carbonyl compounds in the presence of a catalytic amount of fluoride anion to give silylated propargyl alcohol derivatives.The reaction fails with enolizable enones and cyclopentanone.The reaction of bis(trimethylsilyl)acetylene does not stop at the stage of monoadduct, and affords a considerable amount of symmetric bisadduct. (Trimethylsilyl)acetylene attacks 4-t-butylcyclohexanone from the axial side, as other metal acetylides do.Although much slower than the above cases, the reaction of alkynyltrimethylsilanes also proved successful.The reactivities of these (trimethylsilyl)-acetylenes are discussed in terms of the reaction mechanism and the nature of the reactive species, and also compared with those of the silylated enols under similar conditions.
