129803-19-6Relevant academic research and scientific papers
Dual Lewis Acid/Lewis Base Catalyzed Acylcyanation of Aldehydes: A Mechanistic Study
Laurell Nash, Anna,Hertzberg, Robin,Wen, Ye-Qian,Dahlgren, Bj?rn,Brinck, Tore,Moberg, Christina
, p. 3821 - 3829 (2016)
A mechanistic investigation, which included a Hammett correlation analysis, evaluation of the effect of variation of catalyst composition, and low-temperature NMR spectroscopy studies, of the Lewis acid-Lewis base catalyzed addition of acetyl cyanide to prochiral aldehydes provides support for a reaction route that involves Lewis base activation of the acyl cyanide with formation of a potent acylating agent and cyanide ion. The cyanide ion adds to the carbonyl group of the Lewis acid activated aldehyde. O-Acylation by the acylated Lewis base to form the final cyanohydrin ester occurs prior to decomplexation from titanium. For less reactive aldehydes, the addition of cyanide is the rate-determining step, whereas, for more reactive, electron-deficient aldehydes, cyanide addition is rapid and reversible and is followed by rate-limiting acylation. The resting state of the catalyst lies outside the catalytic cycle and is believed to be a monomeric titanium complex with two alcoholate ligands, which only slowly converts into the product.
Ionic liquid [bmim]BF4 as an efficient and recyclable reaction medium for the synthesis of O-acetyl cyanohydrin via one-pot condensation of aldehyde, TMSCN, and Ac2O
Shen, Zhi-Liang,Ji, Shun-Jun
experimental part, p. 808 - 818 (2009/08/08)
Ionic liquid [bmim]BF4 has been demonstrated to be an efficient and environmentally friendly reaction medium as well as reaction promoter for the synthesis of O-acetyl cyanohydrin via one-pot condensation of aldehyde, TMSCN, and Ac2O without Lewis acid or
DABCO-Mediated Synthesis and Biological Activity of Cyanihydrin Esters
Hoffmann, H. M. R.,Ismail, Z. M.,Hollweg, Reiner,Zein, Abdul R.
, p. 1807 - 1810 (2007/10/02)
Cyanohydrin esters 1-31 have been prepared from α-ketonitriles and aldehydes using DABCO (1,4-diazabicyclooctane) as nucleophilic acylation catalyst.The modofied piperonal 8 was found to inhibit the formation of thromboxane synthetase.
