20731-93-5

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 495-40-9 propiophenone 
• 927-77-5 n-propylmagnesium bromide 
• 93-55-0 1-phenyl-propan-1-one 
• 106-94-5 propyl bromide 
• 589-38-8 n-hexan-3-one 
• 100-58-3 phenylmagnesium bromide 
• 2234-82-4 1-propylmagnesium chloride 
• 29443-43-4 propionaldehyde hydrazone 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 100-52-7 benzaldehyde 

Downstream Products

• 94602-56-9 hex-2-ene-3-ylbenzene 
• 20247-88-5 3-phenyl-hex-3ξ-ene 
• 4468-42-2 3-phenylhexane 
• 59734-80-4 3-(<4-³H>-phenyl)-hexan 
• 59734-89-3 3-(4-Bromphenyl)-hexan 
• 59734-88-2 3-(2-Bromphenyl)-hexan 
• 1036760-43-6 3-phenylhexan-3-yl-4-nitrobenzoate 
• 59734-79-1 3-(<2-³H>-phenyl)-hexan 
• 4456-99-9 3-hexylcyclohexane 
• 87839-99-4 1-(1-Ethylbutyl)-4-(1-ethyl-1-phenylbutyl)benzol 
• 58977-30-3 (1-Azido-1-ethyl-butyl)-benzene 

Relevant academic research and scientific papers

Synergistic Relay Reactions To Achieve Redox-Neutral α-Alkylations of Olefinic Alcohols with Ruthenium(II) Catalysis

Herein, we report a ruthenium-catalyzed redox-neutral α-alkylation of unsaturated alcohols based on a synergistic relay process involving olefin isomerization (chain walking) and umpolung hydrazone addition, which takes advantage of the interaction between the two rather inefficient individual reaction steps to enable an efficient overall process. This transformation shows the compatibility of hydrazone-type “carbanions” and active protons in a one-pot reaction, and at the same time achieves the first Grignard-type nucleophilic addition using olefinic alcohols as latent carbonyl groups, providing a higher yield of the corresponding secondary alcohol than the classical hydrazone addition to aldehydes does. A broad scope of unsaturated alcohols and hydrazones, including some complex structures, can be successfully employed in this reaction, which shows the versatility of this approach and its suitability as an alternative, efficient means for the generation of secondary and tertiary alcohols.

Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model

The chelation-control model explains the high diastereoselectivity obtained in additions of organometallic nucleophiles to α-alkoxy ketones but fails for reactions of allylmagnesium halides. Low diastereoselectivity in ethereal solvents results from no chelation-induced rate acceleration. Additions of allylmagnesium bromide to carbonyl compounds are diastereoselective using CH2Cl2 as the solvent even though rate acceleration is still absent. Stereoselectivity likely arises from the predominance of the chelated form in solution. Therefore, a revised chelation-control model is proposed.

New ligands and structural insights into the catalytic asymmetric addition of organozinc reagents to ketones

The catalytic asymmetric addition of alkyl groups to ketones has received considerable attention. Outlined herein is the synthesis of two new ligands based on the C2-symmetric 11,12-diamino-9,10-dihydro-9,10- ethanoanthracene. The scope of the new ligands has been evaluated in the catalytic asymmetric addition of diethylzinc to a variety of ketones. Enantioselectivities as high as 99% have been achieved. The structures of two of these ligands have been determined by X-ray crystallography and are compared with related structures. Additionally, the structure of a titanium complex bound to a bis(sulfonamide) diol ligand is reported.

Study of syntheses and specific rotations of (S)-3-phenylhexan-3-ol and its derivatives

Tertiary alcohols, 3-phenylhexan-3-ol and 3-methylhexane-3-ol, and their derivatives were synthesized. The reaction conditions of the esterification of the tertiary alcohol with 2-NO2PhCO2Cl and 4-NO2PhCO2Cl were optimized. The absolute configuration of the derivative from (S)-3-phenylhexan-3-ol was identified by X-ray study and computational methods. Experimental results confirmed the computational specific rotation predictions by DFT-based and matrix methods.

13C NMR spectroscopic comparison of sterically stabilized meta and para-substituted o-tolyldi(adamant-l-yl)methyl cations with conjugatively stabilized benzyl cations

A series of meta- and para-substituted anti-o-tolyldi(adamant-1-yl)methyl cations has been generated by reaction of anti-o-tolyldi(adamant-1-yl)methanols with trifluoroacetic acid in chloroform. 13C NMR spectroscopy indicates small but significant variations in the chemical shifts of the charged carbon and its nearest neighbours on the adamantyl groups, and departures from additivity of substituent effects on the shifts of the aromatic carbons. Previous work on the closely related di(adamant-1-yl)benzyl cations is discussed. Comparison with data on aryl-substituted carbocations in superacid media reveals marked differences in the aromatic carbon shifts in the two types of carbocation. The dihedral angle between aryl and carbocation planes in aryldi(adamant-1-yl)methyl cations is estimated to be about 60°.

Thermolabile Hydrocarbons, XX. Synthesis, Structure, and Strain of Sym. Tetraalkyl-1,2-diarylethanes

The syntheses of 18 1,1,2,2-tetraalkyl-1,2-diarylethanes 1 - 4 by dimerisation procedures starting with 10 - 13 are reported.In the absence of p-substituents X and with increasing alkyl side chains the α,p-dimers 6 or their aromatic counter parts 7 are obtained besides or instead of 1.The relationships between strain enthalpy Hs, bond lengths, bond angles, torsional angles, and rotational barrier are discussed on the basis of force field calculations.They are supported by two additional experimental structure determinations by X-ray diffraction.