42361-33-1

Upstream product

• 542-69-8 1-iodo-butane 
• 28744-77-6 sodium diethyl-2-phenylmalonate 
• 100-44-7 benzyl chloride 
• 145345-04-6 C₁₁H₁₉O₄^(1-) 
• 133-08-4 diethyl butylmalonate 
• 104856-46-4 benzyl 2,3,4,5,6-pentafluorobenzoate 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 109-65-9 1-bromo-butane 

Downstream Products

• 159213-11-3 (R)-2-Benzyl-hexanal 
• 7500-73-4 (±)-2-benzyl-1-hexanol 
• 7500-73-4 (2R)-2-Benzyl-1-hexanol 
• 114409-87-9 (2S)-2-Benzyl-1-hexanol 
• 225917-33-9 2-benzyl-hexanoic acid amide 
• 57772-77-7 ethyl 2-butyl-3-phenylpropanoate 
• 4375-38-6 benzyl-butyl-malonic acid 

Relevant academic research and scientific papers

Synthesis and olfactory evaluation of optically active β-alkyl substituted γ-lactones and whiskey lactone analogues

Optically active β-alkyl substituted γ-lactones and whiskey lactone analogues were synthesized, and the odor properties were evaluated. During the preparation of the chiral intermediates, we found good reaction conditions for the highly enantioselective esterification of 3-arylmethyl-2-methyl-1-propanols to kinetically resolve them. The results of the olfactory evaluations of the synthesized lactones revealed that the alkyl groups on the γ-lactone rings played an important role for the odor profiles.

Nickel-Catalyzed Benzylic Substitution of Benzyl Esters with Malonates as a Soft Carbon Nucleophile

The nickel-catalyzed benzylic substitution of benzyl alcohol derivatives with a soft carbon nucleophile is extremely rare compared to that with a hard carbon nucleophile. We have achieved the nickel-catalyzed benzylic substitution of benzyl esters with malonates as a soft carbon nucleophile. Primary and secondary benzyl 2,3,4,5,6-pentafluorobenzoates as well as a wide variety of malonate derivatives were well tolerated in the nickel-catalyzed reaction, providing the corresponding alkylation products in 46-86% yields (34 examples). Additionally, we propose a possible reaction mechanism that would undergo via the ??1- A nd ??3-benzylnickel intermediates.

Oxidation potential as a measure of the reactivity of anionic nucleophiles. Behaviour of different classes of nucleophiles

Anodic peak potentials for 42 anionic nucleophiles are reported along with the rate constants for the reactions of the anions with benzyl chloride.By comparing these rate constants with those of the reactions of outer-sphere electron-transfer reagents (radical anions), it has been demonstrated that the reactions of the anions with benzyl chloride are typical single-step SN2 reactions as opposed to a two-step process comprising dissociative single electron transfer (SET) to benzyl chloride followed by radical combination.The data suggest that very electron-rich nucleophilic anions with potentials of -1.5 to -2.2 V (and more negative) with respect to the ferrocenium/ferrocene couple might participate in a SET reaction.The 42 anions studied included representatives of four classes of nucleophiles, viz. sulfur-, carbon-, oxygen- and nitrogen-centred anions.The previously observed correlation of rate constants and anodic peak potential was again found for these anions with the most reactive species having the most negative peak potentials.Correlations by class indicate that the sensitivity of rate constants to changes in peak potential is greatest (and equivalent) for the sulfur-, carbon- and oxygen-anions and for representatives with the same peak potential, the rate constants by class follow the order sulfur > carbon > oxygen.The nitrogen nucleophiles show a significantly lower sensitivity of rate constant to changes in peak potential than do the other three classes.