33493-90-2

Upstream product

• 23708-48-7 pentamethylenebis(magnesium bromide) 
• 4192-77-2 ethyl cinnamate 
• 253797-51-2 1-[(2-hydroxy-2-phenyl-1-phenylsulfanyl)ethyl]cyclohexanol 
• 108-86-1 bromobenzene 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 1004-22-4 (phenylethynyl)sodium 
• 140-10-3 (E)-3-phenylacrylic acid 
• 108-93-0 cyclohexanol 
• 1940-19-8 1-vinylcyclohexanol 
• 108-94-1 cyclohexanone 
• 1192-37-6 methylenecyclohexane 
• 148368-51-8 2-methyl-3-phenyl-5-spirocyclohexylisoxazolidine 
• 3376-23-6 C-phenyl-N-methylnitrone 
• 3561-67-9 bis(phenylthio)methane 

Downstream Products

• 68826-53-9 (E)-(2-(cyclohex-1-en-1-yl)vinyl)benzene 
• 33493-91-3 trans-1-Phenyl-2-(1'-methoxycyclohexyl)ethylen 

Relevant academic research and scientific papers

A Conformational Study of Two Jet-Cooled Conjugated Styryl Cyclohexenes

The S1 0 resonance-enhanced ionization spectra are presented for two jet-cooled cyclohexene compounds, 2-(trans-β-styryl)-1,3,3-trimethylcyclohexene and 1-(trans-β-styryl)-cyclohexene, in which the cyclohexene ring is formally conjugated to a styryl group.In the trimethyl-substituted derivative, strong steric interactions between the cyclohexene ring and styryl group are present, similar to those found in the retinal system, which significantly influence the ground-state molecular conformation.Both of these styryl cyclohexenes exhibit spectra that are dominated by an intense origin transition, indicating little change in molecular geometry between the two electronic states.In 2-(trans-β-styryl)-1,3,3-trimethylcyclohexene, two peaks at 34 441 and 34 452 cm-1 are assigned origin transitions of different molecular conformations on the basis of power saturation experiments.A relationship between the origin transition energy and the torsional angle of the cyclohexene ring is derived and then used to determine the ground-state equilibrium torsional geometry for both compounds.The two conformations of 2-(trans-β-styryl)-1,3,3-trimethylcyclohexene are determined to have the cyclohexene ring tilted +/- 73 deg C out of the plane of the conjugated styryl system while in 1-(trans-β-styryl)-cyclohexene the cyclohexene double bond is found to be 14-21 deg from a planar, fully conjugated conformation.

Transition-Metal Catalyzed Stereoselective γ-Arylation and Friedel-Crafts Alkylation: A Concise Synthesis of Indenes

A highly stereoselective [Pd]-catalyzed arylation of tert-alkenols, is presented and applied to the synthesis of indenes using intramolecular Friedel–Crafts alkylation sequence. The initial Heck reaction is performed by using water as the green solvent. A simple acid triggers intramolecular alkylation in short reaction times at room temperature. Notably, indenes have been accomplished using a single column chromatography technique.

Stereo-controlledanti-hydromagnesiation of aryl alkynes by magnesium hydrides

A concise protocol foranti-hydromagnesiation of aryl alkynes was established using 1?:?1 molar combination of sodium hydride (NaH) and magnesium iodide (MgI2) without the aid of any transition metal catalysts. The resulting alkenylmagnesium intermediates could be trapped with a series of electrophiles, thus providing facile accesses to stereochemically well-defined functionalized alkenes. Mechanistic studies by experimental and theoretical approaches imply that polar hydride addition from magnesium hydride (MgH2) is responsible for the process.

Silver-catalyzed decarboxylative C(sp2)-C(sp3) coupling reactions: Via a radical mechanism

A silver catalyzed decarboxylative C(sp2)-C(sp3) coupling of vinylic carboxylic acids with alcohols, alkylbenzenes, cycloalkanes and cyclic ethers was developed by using DTBP as an oxidant. This reaction tolerates a wide range of substrates, and products are obtained in good to excellent yields. The reaction also shows good stereoselectivity, and only trans-isomers are obtained. In addition, a radical pathway would be involved to facilitate this decarboxylative C(sp2)-C(sp3) coupling reaction.

N-heterocyclic carbene-catalyzed hydrosilylation of styryl and propargylic alcohols with dihydrosilanes

Reducing alkenes to tears: Addition of structurally diverse N-heterocyclic carbenes (NHCs) to silicon allows the reduction of propargylic and styryl alcohols through an organocatalyzed silylation/direct hydride transfer tandem reaction (see scheme). Catalytic turnover is enabled by the switch to and from hypervalent silicon. This provides a new synthetic application of NHC-main group element complexes. Copyright

Polylithiation of thioethers: A versatile route for polyanionic synthons

The successive reaction of phenyl vinyl thioether (1) with n-butyllithium and an electophile [E1=PhCHO, (CH2)4CO, (CH2)5CO] in THF at - 78°C gives, after hydrolysis, the expected methylenic hydroxy thioethers (2). Deprotonation of 2 with n-butyllithium followed by a DTBB-catalysed lithiation and reaction with a second electrophile [E2=tBuCHO, PhCHO, Me2CO, (CH2)5CO], at - 78°C, gives after hydrolysis the corresponding methylenic diols 3. The same diols can be prepared starting from 1 in a one-pot process without isolation of the hydroxy thioether 2. The same methodology was applied to the cyclopropyl phenyl thioether (4), cyclopropyl 1,3-diols 5 {E1=tBuCHO, PhCHO, [Me(CH2)4]2CO, (CH2)5CO, (CH2)7CO; E2=tBuCHO, Me2CO, (CH2)5CO} being isolated in moderate yields. The successive treatment of bis(phenylthio)methane (7) with: (a) n-butyllithium at 0°C, (b) a carbonyl compound [E1=tBuCHO, Me2CO, Et2CO, (CH2)5CO] at - 40°C, (c) lithium and catalytic amount of DTBB (5%) and (d) a second carbonyl compound [E2=iPrCHO, tBuCHO, Me2CO, Et2CO, (CH2)5CO] both at - 78°C leads, after hydrolysis, to the expected dihydroxy thioethers 8. When after step (d), a second DTBB-catalysed lithiation is performed at temperatures ranging between - 78 and 20°C, the corresponding allylic alcohols 9 were isolated. Finally, treatment of alcohols 9 with a few drops of 6 M hydrochloric acid gives dienes 10 in almost quantitative yields.

Preparation of oxetanes by 4-endo trig electrophilic cyclisations of cinnamic alcohols

The reaction of substituted cinnamic alcohols with bis(sym-collidine)bromine(I) hexafluorophosphate was examined. In general no oxetane was obtained when a substituent was fixed on the carbon-carbon double bond. However, oxetanes were formed in high yield

Microwave-assisted one-pot hydrostannylation/Stille couplings.

In a fraction of the time required by conventional methods, microwave-accelerated one-pot hydrostannylation/Stille coupling allows 1-alkynes to be efficiently transformed into 1,3-dienes or styrenes.

Methane-derived polyanionic synthons from bis(phenylthio)methane

Successive treatment of bis(phenylthio)methane (1) with (a) n-butyllithium at 0°C, (b) a carbonyl compound [(t)BuCHO, Me2CO, Et2CO, (CH2)5CO] at -40°C, (c) lithium and a catalytic amount of DTBB (5%) and (d) a s

Selectivity on the reaction of vinylic tellurides with butyllithium in the presence of carbonyl compounds.

The treatment of isomeric vinylic tellurides 5-7 with butyllithium in THF at -78 °C in the presence of a carbonyl compound such as benzaldehyde or cyclohexanone was studied. High selectivity of the attack at the tellurium atom was observed. In most cases, the corresponding allylic alcohol was obtained as the only (or major) product instead of the alcohols derived by the 1,2 addition of BuLi at the carbonyl compound. Similar results were obtained using the ketenetelluroacetal 14 instead of the vinylic monotellurides.