15785-29-2

Upstream product

• 101-97-3 Ethyl 2-phenylethanoate 
• 103-82-2 phenylacetic acid 
• 40638-92-4 1,1-dideuterio-2-phenylethanol 

Downstream Products

• 934-85-0 styrene-d2 
• 1208609-82-8 2,2-dideutero-3-phenylpropane dithiolic acid 
• 19136-97-1 α-dideuterated 3-phenyl propionic acid 
• 29372-33-6 α,α-dideuterated hydrocinnamaldehyde 
• 17428-98-7 2-[D₂]-3-phenylpropan-1-ol 
• 54845-21-5 (3-bromopropyl-2,2-d₂)benzene 
• 114124-97-9 1,1-dideuterio-2-phenylethyl radical 

Relevant academic research and scientific papers

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides

A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which pro

Vicinal Diboration of Alkyl Bromides via Tandem Catalysis

Vicinal diboration of alkyl bromides via tandem catalysis is reported. The reported reaction exhibits a broad substrate scope, good functional group compatibility, and regioselectivity. Moreover, it shows good practicality due to the easy accessibility of alkyl bromides in combination with diverse transformations of diboronates. Mechanism study indicates that terminal alkenes are generated selectively through nickel-catalyzed dehydrohalogenation of alkyl bromides followed by base/MeOH promoted diboration process to provide 1,2-diboration products.

Alkene migration to the end-terminal carbon bearing a phenyl group over a chiral siloxy carbon center in Heck reaction

Abstract The Heck reaction of aryl bromide with a terminal alkene substrate having a chiral center at the allylic position and a phenyl substituent at another terminal carbon is reported. An alkene migration to the phenyl-substituted end carbon is observed, along with the typical Heck reaction. This zipper-type migration occurs through multiple internal carbon bonds, and the stereochemistry of the internal chiral center is completely retained during this process.

Diagnostic fragmentations of adducts formed between carbanions and carbon disulfide in the gas phase. A joint experimental and theoretical study

Selected carbanions react with carbon disulfide in a modified LCQ ion trap mass spectrometer to form adducts, which when collisionally activated, decompose by processes which in some cases identify the structures of the original carbanions. For example (i) C6H5- + CS 2→ C6H5CS2-→ C6H5S- + CS, occurs through a 3-membered ring ipso transition state, and (ii) the reaction between C6H 5CH2- and CS2 gives an adduct which loses H2S, whereas the adduct(s) formed between o-CH 3C6H5- and CS2 loses H2S and CS. Finally, it is shown that decarboxylation of C 6H5CH2CH2CO2- produces the β-phenylethyl anion (PhCH2CH2 -), and that this thermalized anion reacts with CS2 to form C6H5CH2CH2CS2 - which when energized fragments specifically by the process C 6H5CH2CH2CS2 -→ C6H5CH2-CHC(S)SH → [(C6H5CH2CHCS) -SH] → C6H5CH2CCS- + H2S. Experimental findings of processes (ii) and (iii) were aided by deuterium labelling studies, and all reaction profiles were studied by theoretical calculations at the UCCSD(T)/6-31+G(d,p)//B3LYP/6-31+G(d,p) level of theory unless indicated to the contrary.

Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with α-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl (1S,2S)-2- phenylcyclopropanecarboxylates (the 1-d-3-13C, 1,(3S)-d2, 1,2,(3S)-d3, and 1,3,3-d3 isotopomers) of better than 99% ee have been realized. The Royal Society of Chemistry 2006.

On the Generation and Characterization of the Spirooctadienyl Anion in the Gas Phase

Three routes have been explored in both a high-pressure chemical ionization (CI) source and a low-pressure Fourier transform ion cyclotron resonance (FT-ICR) cell to generate the spirooctadienyl anion in the gas phase: (i) proton abstraction from spiroocta-4,6-diene; (ii) expulsion of trimethylsilyl fluoride by phenyl ring participation following fluoride anion attack upon the silicon centre of 2-phenylethyl trimethylsilane; and (iii) collisionally induced dissociation (CID) of the carboxylate anion of 3-phenylpropanoic acid via carbon dioxide loss.From comparison of the CID spectra of various reference (1-) ions with those of the (1-) ions with those of the (1-) ions which could be generated via the routes (i) and (iii) in the CI source it can be concluded that only the third route yields a (1-) in whose CID spectrum is not inconsistent with the one expected for the spirooctadienyl anion.In the FT-ICR cell (1-) ions are generated along all three routes; their structures have been identified by specific ion-molecule reactions and appear to be different.Route (i) yields an α-methyl benzyl anion, probably due to isomerization within the ion-molecule complex formed.An ortho-ethylphenyl anions is formed along route (ii), presumably due to an intramolecular ortho proton abstraction in the generated trimethylsilyl fluoride solvated 2-phenylethyl primary carbanion.The (1-) ion formed along route (iii) shows reactions similar to those of the 1,1-dimethylcyclohexadienyl anion which is structurally related to the spirooctadienyl anion.Furthermore, the (1-) ion generated via route (iii) reacts with hexafluorobenzene under expulsion of only one hydrogen fluoride molecule which contains exclusively one of the original phenyl ring hydrogen atoms.On the basis of all these observations it is therefore quite likely that the spirooctadienyl anion is formed by collisionally induced decarboxylation of the 3-phenylpropanoic acid carboxylate anion and can be a long-lived and stable species in the gas phase.