6124-66-9

Upstream product

• 75-09-2 dichloromethane 
• 98-86-2 acetophenone 
• 28478-27-5 4-(2-phenyl-propenyl)-morpholine 
• 51673-52-0 N-chloro-N'-tosylbenzamidine 
• 113676-38-3 N-chloro-N'-(4-nitrobenzenesulfonyl)-benzamidine 
• 34713-70-7 2-Phenylpropanal 
• 121034-40-0 2-Phenyl-2-phenylselanyl-propionaldehyde 
• 121034-41-1 2-(4-Chloro-phenylselanyl)-2-phenyl-propionaldehyde 
• 24401-44-3 β-Piperidino-α-methyl styrene 
• 2156-71-0 N-chloropiperidine 
• 19733-68-7 N-chloropyrrolidine 
• 107116-39-2 Pentachloro<2-phenyl-1-(1-pyridinio)propoxy>antiomonat 

Downstream Products

• 136846-88-3 rac-2-tert-Butyl-2,5-dihydro-5-methyl-5-phenyloxazol 
• 161869-72-3 2-Chloro-2-phenyl-propionaldehyde O-methyl-oxime 
• 25076-75-9 2-phenyl-2-piperidin-1-yl-propionaldehyde 
• 1418369-63-7 (RS)-5-phenyl-2,2,5-trimethyl-2,5-dihydro-1,3-thiazole 
• 81171-24-6 N-isopropyl-α-chloro-α-phenylaldimine 
• 17325-55-2 (+/-)-2-chloro-2-phenyl-propionic acid 

Relevant academic research and scientific papers

Investigation of the Organocatalytic Chlorination of 2-Phenylpropanal

Results of an examination of the organocatalytic enantioselective α-chlorination of 2-phenylpropanal are described. Synthetic investigation including the screening of primary and secondary aminocatalysts, many different reaction conditions, and other α-br

Trichloromethanesulfonyl chloride: A chlorinating reagent for aldehydes

Trichloromethanesulfonyl chloride (CCl3SO2Cl), a commercially available reagent, has been found to perform efficiently in the α-chlorination of aldehydes, including its catalytic asymmetric version, under very mild reaction conditions. Under our reaction conditions, this compound outperforms typical chlorinating reagents for organic synthesis, facilitates workup and purification of the product, and minimizes the formation of toxic, chlorinated organic waste.

The Rabe amination after a century: Direct addition of N-heterocycles to carbonyl compounds

A catalytic version of the Rabe electrophilic amination is presented. This kind of reaction was originally employed in 1918 in a key step for the conversion of quinotoxine to quinine. Ketones and α-substituted aldehydes give the corresponding α-aminated carbonyl compounds in moderate yield. α,α-Unsubstituted aldehydes give rise to amino ketones via a novel rearrangement.

Synthesis of 1,1-bisphosphono-2-aza-1,3-dienes, a new class of electron-deficient azadienes

1,1-Bisphosphono-2-aza-1,3-dienes are formed by 1,4-dehydrohalogenation of the corresponding N-(bisphosphonomethyl)-α-haloimines in moderate to good yields. The precursors could be formed by condensation of bisphosphono-amines and the corresponding α-haloaldehydes.

Use of phenylselenium trichloride for simple and rapid preparation of α-phenylselanyl aldehydes and ketones

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

α-Imino and α-oximino carbocations. A comparison with α-carbonyl and α-thiocarbonyl carbocations

The σ+ values for the groups m-CH=N-t-Bu and p-CH=N-t-Bu have been determined to be 0.16 and 0.078, respectively. The CH=N-t-Bu group is therefore cation-destabilizing relative to hydrogen when placed in the meta position of a cumyl cation. Although the p-CH=N-t-Bu group is still cation-destabilizing, the effect is reduced by a competing resonance effect when the imino group is placed in the para position. However, when attached directly to a cationic center, this imino group enhances rates relative to α-H. This is interpreted in terms of a cation-stabilizing conjugative effect. The σ+ value of the p-oximino group, p-CH=NOCH3, is -0.03 and indicates that a cation-stabilizing conjugative effect can essentially offset the inductive effect of this electron-withdrawing substituent in a cumyl cation. However, when attached directly to a developing cationic center, this oximino group greatly enhances cation formation rates relative to hydrogen. This group is even more cation-stabilizing than the methyl group. Studies on systems of type ArCH(OMs)C(NOCH3)Ph, where the oximino group can be syn or anti to the developing cationic center, indicate the existence of isomeric α-oximino cations, with the anti cations forming faster than the syn cations. Computational studies at the MP2/6-31G** level support the idea of extensive conjugative stabilization of α-oximino cations. Despite extensive mesomeric stabilization of α-oximimo cations, the primary cation +CH2CH=NOCH3 cannot be solvolytically generated since nucleophilic solvent displacement processes dominate. Stabilities of a series of cations of type +CH2X, where X is a formal electron-withdrawing group, have been evaluated by ab initia methods. Isodesmic reactions indicate a stability order of α-CHNOCH3 ～ CH=CH2 > CHNHCH3 > CHS > CHO ～ H > CN > NO2.

One-pot conversion of α-substituted arylacetaldehydes into α-dicarbonyl compounds

α-dicarbonyl compounds 7-12 can be easily prepared by reaction of methylene chloride solutions of several α-substituted arylacetaldehydes 1-6 with a slight excess of tris-(o,p-dibromophenyl) ammoniumyl hexachloro antimonate A.

Synthesis and Reactivity of 3-Oxazolines

3-Oxazolines 1 have been prepared from α-hydroxy aldehydes, ammonia, water and a second oxo compound (aldehyde or ketone) in a one-pot reaction.Carboxylic acid chlorides add to the azomethine bond of 1 to yield 3-acyl-4-chlorooxazolidines 2. 4-Hydroxy and 4-alkoxyoxazolidines 3 are obtained from 2 upon treatment with aqueons sodium hydroxide or alkanol/triethyl amine, respectively.Some oxazolidines 3 are formed with high diastereoselectivity. Key Words: Oxazole, 2,5-dihydro- / Oxazolidine / Acyliminium ion

REACTIVITY OF α-ARYLSELENO-ALDEHYDES TOWARDS HALOGENS AND BENZENESELENENYL CHLORIDE

Chlorination of α-seleno-aldehydes bearing an α-hydrogen gives selenium dichlorides which decompose into α-chloro α-seleno-aldehydes and α-chloroenal.Bromination, in all cases, and chlorination for the other α-seleno-aldehydes lead to the α-halogenoaldehydes.