7661-43-0

Upstream product

• 34713-70-7 2-Phenylpropanal 
• 693-04-9 butyl magnesium bromide 
• 542-69-8 1-iodo-butane 
• 110-62-3 pentanal 
• 492-37-5 hydratropic acid 
• 109-65-9 1-bromo-butane 

Downstream Products

• 7661-44-1 2-phenyl-3-heptanone 

Relevant academic research and scientific papers

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

Samarium(II) triflate as a new reagent for the grignard-type carbonyl addition reaction

On treatment of a THF solution of Sm(OTf)3 with 1 equiv of an organolithium or organomagnesium reagent at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)2] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of 2-phenylethyl iodide in the presence of HMPA. The Sm(OTf)2 reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)2 gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)2 reagent.

Effects of additives on cuprate 1,4-additions: Gilman reagents in the presence of Me3SiCN

Chemical and spectroscopic studies on Gilman cuprates R2CuLi·LiI in the presence of TMS-CN reveal the lack of independence of these species in THF solutions. A potential role for this additive in enhancing rates and yields of 1,4-, as well as 1,2-additions, is suggested.

Zirconium Mediated Regioselective Carbon-Carbon Bond Formation Reactions

Reactions of zirconocene-alkene complexes with aldehydes gave alcohols as coupling products after hydrolysis.The carbon-carbon bond formation proceeded at C1 carbon of alkenes, in sharp contrast to the reactions of alkene-alkene coupling on zirconium.A similar alcohol was also obtained by the reaction of zirconacyclopentane with aldehyde after hydrolysis.Treatment of (C5Me5)2ZrEt2 with styrene gave 2-phenylbutane after hydrolysis contrary to the case of Cp2ZrEt2 which afforded 1-phenylbutane.

Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: Myth and reality

The reaction of racemic 2-phenylpropanal with methyl- and n-butyllithium was studied in detail. Factors such as temperature, solvent, rate of addition, presence of salts, scale-up and source of reagents were carefully examined. Cram-selectivities of 90-94

EFFECT OF GEGENIONS ON ORGANOCUPRATE REACTIVITY/SELECTIVITY: HIGHER ORDER, MIXED LITHIO-SODIO CYANOCUPRATES

Several different types of reactions characteristic of organocuprates have been studied using reagents RTRRCu(CN)LiNa derived from CuCN and one equivalent each of an organolithium (RTLi) and organosodium (RRNa) species.

Stereoselective Oxidation of β-Methyl-sec-alcohols and α-Methylketones by Corynebacterium equi IFO 3730

The enzyme system of Corynebacterium equi IFO 3730 catalyzed the diastereo-selective oxidation of β-methyl-sec-alcohols.For example, only the erythro isomer of 5-methyl-6-tetradecanol was oxidized to the corresponding ketone, the threo-alcohol remaining.M