50735-77-8Relevant academic research and scientific papers
Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes
West, Michael S.,Mills, L. Reginald,McDonald, Tyler R.,Lee, Jessica B.,Ensan, Deeba,Rousseaux, Sophie A. L.
supporting information, p. 8409 - 8413 (2019/10/14)
Cyclopropylamines are prevalent in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring closure to generate the cyclopropylamine. We have also observed that cyclopropylamine cis/trans-isomerization occurs in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic cosolvent.
Synthesis of 3-arylcoumarins through N-heterocyclic carbene catalyzed condensation and annulation of 2-chloro-2-arylacetaldehydes with salicylaldehydes
Jiang, Yuansong,Chen, Wanzhi,Lu, Weimin
supporting information, p. 3669 - 3676 (2013/05/08)
The condensation reaction of 2-chloro-2-arylacetaldehyde with salicylaldehyde catalyzed by N-heterocyclic carbene (NHC) leading to 3-arylcoumarin was studied. A number of 3-arylcoumarin derivatives were obtained in good to excellent yields via this umpolung reaction. This reaction is facile and experimentally simple and mild.
Use of phenylselenium trichloride for simple and rapid preparation of α-phenylselanyl aldehydes and ketones
Houllemare, Didier,Ponthieux, Sylvain,Outurquin, Francis,Paulmier, Claude
, p. 101 - 106 (2007/10/03)
α-Phenylselanyl aldehydes are prepared on a large scale by reaction of PhSeCl3 with the corresponding aldehydes in acetonitrile without isolation of the intermediate dichloro adducts. This method has been applied to α-phenylselanyl ketones deri
2,2-DICHLOROALDEHYDES FROM ALDEHYDES AND ALCOHOLS BY CHLORINATION IN DIMETHYLFORMAMIDE
Buyck, L. De,Verhe, R.,Kimpe, N. De,Courtheyn, D.,Schamp, N.
, p. 441 - 458 (2007/10/02)
A method is described for the synthesis of α,α-dichloroaldehydes, free from monochloroaldehyde, by chlorination of aldehydes or alcohols in dimethylformamide at 40-90 deg C.Results are reported for : (yield percent) propanal (90), butanal (78), pentanal (78), 3-methylbutanal (90), propanol (64), butanol (78), 3-methylbutanol (52), pentanol (66), 3,3-dimethylbutanol (86), hexanol (66), 2-phenylethanol (51), 3-phenylpropanol (54), 1,5-pentanediol , 1,6-hexanediol .Oxidative conversion (KMnO4, K2Cr2O7, H2O2-NaHCO3) into α,α-dichlorocarboxylic acids and methyl esters is discussed.
