2-acetylfuran Research Articles

Hydrodeoxygenation of 2-furyl methyl ketone as a model compound of algal Saccharina Japonica bio-oil using iron phosphide catalyst

We report the hydrodeoxygenation of 2-furyl methyl ketone over iron phosphide catalyst to reform the C6 structure into C7 compounds with higher octane ratings. High conversion and yield were achievable from the reaction at 400°C when 5wt% Fe2P/γ-Al2O3 catalyst calcined at 600°C was used. High calcination temperature and reaction temperature are the favorable conditions to achieve high conversion in the reaction. The highest conversion of 92.60% was achieved with 2-allyl furan yield of 79.34% and methyl cylcohexane yield of 13.26% in the liquid phase and 100% carbon dioxide in the gas phase.

Spray pyrolysis synthesis of γ-Al2O3 supported metal and metal phosphide catalysts and their activity in the hydrodeoxygenation of a bio-oil model compound

In this study, spherical γ-Al2O3 supported metal and metal phosphide (Ni, Co, Ni2P and CoP) catalysts were successfully prepared by combining sol-gel and spray pyrolysis methods. First boehmite sol was prepared based on the Yoldas process and then the corresponding metal salts were added to the sol at the desired concentration, followed by spray pyrolysis of the mixed solution. As the well-mixed solution was transformed to spherical γ-Al2O3 supported metal and metal phosphide catalysts during spray pyrolysis process, the metal species were uniformly distributed in the mesoporous γ-Al2O3 supports. The product catalysts were investigated under different conditions for hydrodeoxygenation of bio-oil model compound, 2-furyl methyl ketone (FMK), which is the main component of the bio-oil product from pyrolysis of Saccharina japonica. Among the investigated catalysts, the 10wt% Ni/γ-Al2O3 catalyst after calcination at 800°C showed the highest FMK conversion of 83.02% at the reaction temperature of 400°C. The gas and liquid products were analyzed by gas chromatography (GC) with TCD/FID detectors and GC–MS, respectively, to determine the product compositions.

Experimental and kinetic modeling studies of low-pressure premixed laminar 2-methylfuran flames

Depletion and overconsumption of the traditional fossil fuels necessitate the searching of renewable energies and alternative fuels. With its similar properties to those of gasoline, 2-methylfuran (MF) can be used as an alternative fuel or fuel additive directly in the engines. In this work, low-pressure laminar premixed MF/O2/Ar flames with equivalence ratios of 0.80, 1.00, and 1.50 were studied to investigate the flame structure of MF. Synchrotron vacuum ultraviolet photoionization mass spectrometry was used for the measurements of the mole fractions of the flame species. A revised MF mechanism based on that of Somers et al. was used to analyze the reaction pathways of MF, combining the formation and consumption reactions of some key species, such as 2-furylmethyl, propargyl, 1-oxo-1,3,4-pentatriene, 1-oxo-1,3-butadiene, acrolein, and methyl vinyl ketone, etc. The current mechanism may well predict the H-addition products of MF, i.e., 1-oxo-1,3-butadiene and furan, but under-estimate the H-abstraction products of MF, i.e., 2-furylmethyl and 1-oxo-1,3,4-pentatriene. As to the OH-addition products of MF, acrolein and methyl vinyl ketone, the former one is over-predicted. This can be improved by addressing the effect of the MF structure on the OH-addition reactions, taking into account both formation and consumption of these two species.

Ultra-trace analysis of furanic compounds in transformer/rectifier oils with water extraction and high-performance liquid chromatography.

A novel approach for the determination of parts-per-billion level of 5-hydroxymethyl-2-furaldehyde, furfuryl alcohol, furfural, 2-furyl methyl ketone, and 5-methylfurfural in transformer or rectifier oils has been successfully innovated and implemented. Various extraction methods including solid-phase extraction, liquid-liquid extraction using methanol, acetonitrile, and water were studied. Water was by far the most efficient solvent for use as an extraction medium. Separation of the analytes was conducted using a 4.6 mm × 250 mm × 3.5 μm Agilent Zorbax column while detection and quantitation were conducted with a variable wavelength UV detector. Detection limits of all furans were at 1 ppb v/v with linear ranges range from 5 to 1000 ppb v/v with correlation coefficients of 0.997 or better. A relative standard deviation of at most 2.4% at 1000 ppb v/v and 7.3% at 5 ppb v/v and a recovery from 43% to 90% depending on the analyte monitored were obtained. The method was purposely designed to be environmental friendly with water as an extraction medium. Also, the method uses 80% water and 20% acetonitrile with a mere 0.2 mL/min of acetonitrile in an acetonitrile/water mixture as mobile phase. The analytical technique has been demonstrated to be highly reliable with low cost of ownership, suitable for deployment in quality control labs or in regions where available analytical resources and solvents are difficult to procure.

Characterization of interphase volatile compounds in Chinese Luzhou-flavor liquor fermentation cellar analyzed by head space-solid phase micro extraction coupled with gas chromatography mass spectrometry (HS-SPME/GC/MS)

This study aimed to investigate volatile compounds characteristics of Pit mud (PM), Zaopei (ZP), Huangshui (HS) in Chinese Luzhou-flavor liquor fermentation cellar by HS-SPME/GC/MS. Results indicated that pit age and spatial position had a stronger effect on volatiles than physicochemical properties. A total of 59 volatiles had been identified, and phenylethyl alcohol, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid, ethyl lactate, ethyl hexanoate, ethyl hexadecanoate, ethyl linoleate and ethyl elaidate were dominant, accounting for roughly 66.30%. Additionally, the total level of volatiles significantly increased from upper layer (U) to under layer (D), except for 2-year-MPM and 40-year-MZP, and 40-year-DPM (834.14 mg/kg) had the highest content. PCA explanation plane primarily revealed the main differentiation based on their loading plot values. Results of PLS-DA showed 4-methylphenol and gamma-nonanolactone were correlated with 2-year-PM. In addition to ethyl phenylacetate, ethyl hexanoate, furfuryl hexanoate, ethyl nonanoate, perhydrofarnesyl acetone and 2-acetyl furan were associated with 40-year-PM. Isoamyl hexanoate, octyl octanoate, benzaldehyde and 2-nonenal were with 10-year-PM. 3-methyl-1-butanol, ethyl lactate, ethyl hydrocinnamate and 3-furancarboxaldehyde were related to 2-year-ZP, while ethyl decanoate and ethyl linolenate were relevant to 10-year-ZP. No specific compounds for 40-year-ZP and HS samples were found.

Copper(II) Complexes with N,O-Donor Ligands and Ofloxacin Drug as Antibacterial, DNA Interacting, Cytotoxic and SOD Mimic Agent.

The N,O-donor bidentate ligands (L (1) -L (7) ) derived from the reaction between chalcones and pyridinium salt of 2-acetyl furan were synthesized and characterized by IR and NMR spectroscopic techniques. Their complexes [1-7] of Cu(II) were synthesized and characterized by elemental analysis, magnetic measurements, TG analyses, IR and mass spectroscopy. Synthesized complexes were carried out for their biological elucidation using different biological experiments like minimum inhibitory concentration, DNA binding and cleavage study, cytotoxicity, and antiradical activity. Efficient cleavage of pUC19 DNA was observed for all the test complexes than the reference drug. Increase in DNA chain length and hence the relative viscosity as the complexes binds to DNA via intercalative mode and involves a strong stacking interaction between an aromatic chromophore and the DNA base pair.

Quantification of furanic derivatives in fortified wines by a highly sensitive and ultrafast analytical strategy based on digitally controlled microextraction by packed sorbent combined with ultrahigh pressure liquid chromatography

An improved, reliable and powerful analytical strategy based on digitally controlled microextraction by packed sorbent (MEPS) combined with ultrahigh pressure liquid chromatography (UHPLC) was validated for the simultaneous identification and quantification of major furanic derivatives, namely 5-hydroxymethyl-2-furaldehyde (5HMF), 5-methyl-2-furaldehyde (5MF), 2-furaldehyde (2F) and 2-furyl methyl ketone (2FMK), in fortified wines. To enhance the extraction efficiency of the target furanic derivates, several influencing extraction parameters, such as number of loading cycles, nature of elution solvent and elution volume, were evaluated and optimized. In addition the ability of different MEPS sorbent materials, namely C2, C8, C18, SIL, M1, R-AX, R-CX and PGC, were also tested. The optimal analytical conditions involved loading 3×200μL of wine samples through a C8 sorbent in a MEPS syringe placed in the semi-automatic eVolH syringe followed by elution using 200μL MeOH:H2O (95:5, v/v). The furanic derivates separation was achieved using a CORTECS UPLC® C18 analytical column in an ultrafast chromatographic run (within 4min). The method performance was assessed for dry/medium dry (D/MD) and sweet/medium sweet (S/MS) model wines in terms of selectivity, linearity, limit of detection (LOD), limit of quantitation (LOQ), accuracy, precision and matrix effect, using model wine matrix-matched calibration. Good linearity was obtained with a regression coefficient (r2) higher than 0.992. A good precision was attained (RSD<5%) and low LODs were achieved for D/MD (4.5–129.3ngL−1) and S/MS (6.9–285.2ngL−1) model wines. The quantification limits (LOQ) for D/MD model wines ranged from 14.9 to 431.0ngL−1, whereas for S/MS model wines range from 23.1 to 950.5ngL−1. The method also afforded satisfactory results in terms of accuracy, ranging from 74 to 97% for D/MD wines and between 84 and 99% for S/MS wines.The MEPSC8/UHPLC–PDA analytical strategy was successfully applied to analyze furanic derivates in 26 fortified Madeira wines from different types (D/MD, S/MS) and ages. The obtained results revealed the analytical strategy as a suitable tool which combines sensitivity, effectiveness, reduced analysis time and simple analytical procedure. Principal component analysis (PCA) suggested that fortified wines can be organized based on their age on PC1, which are mainly characterized by 5HMF.

Chemical constituents and biological activities of the Purple Perilla essential oil against Lasioderma serricorne

Purple Perilla (Perilla frutescens (L.) Britt.) is an annual herb commonly used as a traditional Chinese medicine for more than 1000 years. This work investigated the chemical composition, insecticidal and repellent activities of the essential oil of Purple Perilla aerial parts against Lasioderma serricorne (Fabricius). Moreover, we also isolated active constituents from the essential oil. The experiment was investigated in 2013 in Beijing. The essential oil of Purple Perilla was obtained by hydrodistillation and a total of 47 components in the essential oil were identified with GC–MS. It was found that the main compounds included carvone (32.55%), perilla aldehyde (20.52%), caryophyllene (9.85%), 2-furyl methyl ketone (7.53%), 2,6-dimethyl-6-(4-methyl-3-pentenyl)-2-norpinene (5.17%), and β-terpinyl acetate (3.41%). With a further isolation, four active constituents were obtained from the essential oil and identified as R-(+)-carvone, perilla aldehyde, 2-furyl methyl ketone, and β-caryophyllene. In the progress of assay, it showed that the essential oil, R-(+)-carvone, perilla aldehyde, and 2-furyl methyl ketone exhibited stronger insecticidal and repellent activities against L. serricorne than β-caryophyllene. The results indicate that the essential oil of Purple Perilla aerial parts and isolated compounds have potential for development into natural insecticides or repellents for control of insects in stored products.

Chemical composition and insecticidal activities of the essential oil of Perilla frutescens (L.) Britt. aerial parts against two stored product insects

The chemical composition of the essential oil of Perilla frutescens (L.) Britt. aerial parts and its insecticidal activity against Tribolium castaneum and Lasioderma serricorne were investigated. The essential oil of P. frutescens was obtained by hydrodistillation and a total of 34 components in the essential oil were identified with GC–MS. It was found that the main compounds included 2-furyl methyl ketone (71.83 %), decahydro-1-methyl-2-methylene-naphthalene (10.47 %), limonene (5.16 %) and caryophyllene (1.66 %). With a further isolation, the two active constituents were obtained from the essential oil and identified as 2-furyl methyl ketone, limonene. In the progress of assay, it showed that the essential oil and 2-furyl methyl ketone exhibited stronger contact and fumigant activities against the two stored product insects than limonene. Moreover, the essential oil and its constituents exhibited the comparable repellency against the two stored product insects, relative to the positive control, DEET. The results indicate that the essential oil of P. frutescens aerial parts and its isolated compounds have potential for development into natural insecticides or fumigants as well as repellents for control of insects in stored grains.

Hydrodeoxygenation of 2-furyl methyl ketone as a model compound in bio-oil from pyrolysis of Saccharina Japonica Alga in fixed-bed reactor

The model ketone of bio-oil, 2-furyl methyl ketone (FMK) or 1-(2-furanyl)-ethanone, which is the main component in Saccharina (Laminaria) Japonica (S. Japonica) pyrolysis products, was successfully upgraded into methyl cyclopentane in the liquid phase and methane in the gas phase. Hydrodeoxygenation (HDO) of FMK over cobalt based phosphide supported on γ-Al2O3 substrates made the conversion possible and highly effective. Complete HDO of FMK into methyl cyclopentane and methane was achievable at 400 °C reaction temperature using CoP/γ-Al2O3 catalyst synthesized with 10 wt.% Co loading and calcined at 500 °C.

Synthesis of some new heterocyclic compounds derived from 2-Chloro-3-formyl quinoline

In this paper the Synthesis of some substituted 2-Chloro-3-formyl quinoline (2a–d) by treating various substituted acetanilide or 1-(4-substituted phenyl) ethanone oxime with POCl3 in dimethyl formamide. It proceeds through Vilsmeier – Haack cyclization. The condensation of 2-chloro-3-formylquinoline with p-Hydroxyacetophenone, 2-acetyl pyridine, 2-acetyl furan or 3-acetyl indole via Claisene– Schmiatcondensations gives quinolinylchalcone (4a – d). Newpyrazoline derivatives were synthesized by condensing the appropriate chalcone (4a) with hydrazine hydrate or phenylhydrazine (10 – 11). Oxazole (12) is reported from compound (4a) and hydroxyl amine hydrochloride is in basic medium. The reaction of chalcone (4a) with urea, thiourea or quinidine hydrochloride gives pyrimidine-2-one (7), pyrimidine-2-thiol (8) or 2- amino pyrimidine (9) respectively.Oxirane (6) prepared from reaction of chalcone (4a) with hydrogen peroxide in basic medium. The reaction of chalcone (4a) with bromine gives dibromide (5). The structures of synthesized compounds were confirmed by spectral and physical methods.

Some new transition metal complexes of bis (2-methyl furfuraldene)-4,4`-methylene bis (cyclohexylamine) ligand

New Fe(II),Co(II),Ni(II),Cu(II) and Zn(II) Schiff base complexes which have the molar ratio 2:1 metal to ligand of the general formula [M2( L) X4] (where L=bis(2-methyl furfuraldene)-4-4`-methylene bis(cyclo-hexylamine) ) were prepared by the reaction of the metal salts with the ligand of Schiff base derived from the condensation of 2:1 molar ratio of 2-acetyl furan and 4-4`-methylene bis (cyclohexylamine). The complexes were characterized by elemental analysis using atomic absorption spectrophotometer ,molar conductance measurements, infrared, electronic spectra,and magnetic susceptibility measurement. These studies revealed binuclear omplexes. The metal(II) ion in these complexes have four coordination sites giving the most expected tetrahedral structure and square planar for Cu(II)ion.

Some new transition metal complexes of bis (2-methyl furfuraldene)-4,4`-methylene bis (cyclohexylamine) ligand

New Fe(II),Co(II),Ni(II),Cu(II) and Zn(II) Schiff base complexes which have the molar ratio 2:1 metal to ligand of the general formula [M2( L) X4] (where L=bis(2-methyl furfuraldene)-4-4`-methylene bis(cyclo-hexylamine) ) were prepared by the reaction of the metal salts with the ligand of Schiff base derived from the condensation of 2:1 molar ratio of 2-acetyl furan and 4-4`-methylene bis (cyclohexylamine). The complexes were characterized by elemental analysis using atomic absorption spectrophotometer ,molar conductance measurements, infrared, electronic spectra,and magnetic susceptibility measurement. These studies revealed binuclear omplexes. The metal(II) ion in these complexes have four coordination sites giving the most expected tetrahedral structure and square planar for Cu(II)ion.

English

A series of 3-(furan-2-yl)-5-(substituted phenyl)-4,5-dihydro-1,2-oxazole derivatives (2a to j) were synthesized by Claisen Schmidt condensation of 2-acetyl furan with different types of aromatic aldehyde, as chalcones and their subsequent cyclization to&nbsp; 4,5-dihydro-1,2-oxazole with hydroxylamine hydrochloride. The chemical structures of the synthesized compounds were confirmed by IR,&nbsp;1H NMR,&nbsp;13C-NMR and mass spectrometric data. This study further involves evaluation of synthesized compounds for antidepressant and antianxiety activities using force swimming test (FST) and elevated plus maze method, respectively. Most of the tested compounds were found to be moderate to significant activities at the dose level of 10 mg/kg, compared to reference drugs imipramine and diazepam, respectively. Compound 4-[3-(furan-2-yl)-4,5-dihydro-1,2-oxazol-5-yl]phenol (2e)&nbsp; emerged as the most potent antidepressant agent acting through monoamine oxidase (MAO) inhibition without any significant neurotoxicity. The molecular docking study were also carried out on the falcipain-2 receptor (PDB id: 2Z5X) for all the compounds and compound 2e was found to occupy in the receptor cavity and forms hydrogen bond and hydrophobic interactions with active residues. &nbsp; Key words:&nbsp;Isoxazoline, Claisen Schmidt condensation, antidepressant, antianxiety.

Investigations of furanic derivatives in transformer oil using ultra‐violet light absorption property

Power transformers are one of the critical components in power system. Insulation plays a promistic role in determining the lifetime of transformers. Insulation used in transformers is of solid and liquid insulation. Solid insulation like kraft paper, press board on degradation process generates furanic derivatives such as 5-methyl furan, 2-acetyl furan, 2-hydroxymethyl furan and 2-furaldehyde. Traditionally, the presence of furanic compounds in transformer oil is determined using high-sperformance liquid chromatography. An effort has been made to estimate the presence of furanic derivatives using artificial neural network (ANN) with the aid of ultra-violet–visible light absorbance property. In ANN system, Levenberg Marquardt back propagation optimisation technique is used to determine the furanic derivatives in transformer oil. Degree of polymerisation of insulation paper and percentage tensile strength of paper remaining has been examined.

Volatile compounds and descriptive odor attributes in umbu (Spondias tuberosa) fruits during maturation

The umbu fruit is appreciated in north and northeast region of Brazil mainly because of its refreshing and acidic flavor. The objective of this work was to determine the volatile compounds in half-ripe and ripe stages of umbu fruit and to identify important characteristic compounds which could contribute for its aroma by performing sniffing evaluation of volatile extracts. The principal volatile compounds identified in the ripe umbu fruit pulp were 4-methyl-3-penten-2-one, ethyl benzene, 1-penten-3-one, 2-acetyl thiazone, p-xylene, limonene, 2,2-dimethyl 4-octenal, 3-hexanol, 2-nonanol, 1-nonanol, 2-pentanol, 2-octanol, 3-methylethyl 2-butanoate, butyl benzoate, 3-allyl cyclohexene, 2-acetyl furan, 2-hexyl furan, β-caryophyllene and methyl pyrazine. A total of 37 volatile compounds were diagnosed with characteristic aroma attributes. The principal volatile compounds which could be responsible for the characteristic aroma of ripe umbu fruit pulp were β-(Z)-ocimene, methyl pyrazine, 2-butyl-thiophene, methyl octanoate, 2-hexyl furan, 2-octanol, (E)-2-cyclohexen-1-one, 3-bromo-cyclohexene, 1-heptanol, 2-nonanol and 1-octanol.

Effectiveness of different solid-phase microextraction fibres for differentiation of selected Madeira island fruits based on their volatile metabolite profile—Identification of novel compounds

A headspace solid-phase microextraction (HS-SPME) procedure based on five commercialised fibres (85 μm polyacrylate – PA, 100 μm polydimethylsiloxane – PDMS, 65 μm polydimethylsiloxane/divinylbenzene – PDMS/DVB, 70 μm carbowax/divinylbenzene – CW/DVB and 85 μm carboxen/polydimethylsiloxane – CAR/PDMS) is presented for the characterization of the volatile metabolite profile of four selected Madeira island fruit species, lemon ( Citrus limon), kiwi ( Actinidia deliciosa), papaya ( Carica papaya L.) and Chickasaw plum ( Prunus angustifolia). The isolation of metabolites was followed by thermal desorption gas chromatography–quadrupole mass spectrometry (GC–qMS) methodology. The performance of the target fibres was evaluated and compared. The SPME fibre coated with CW/DVB afforded the highest extraction efficiency in kiwi and papaya pulps, while in lemon and plum the same was achieved with PMDS/DVB fibre. This procedure allowed for the identification of 80 compounds, 41 in kiwi, 24 in plums, 23 in papaya and 20 in lemon. Considering the best extraction conditions, the most abundant volatiles identified in kiwi were the intense aldehydes and ethyl esters such as (E)-2-hexenal and ethyl butyrate, while in Chicasaw plum predominate 2-hexenal, 2-methyl-4-pentenal, hexanal, (Z)-3-hexenol and cyclohexylene oxide. The major compounds identified in the papaya pulp were benzyl isothiocyanate, linalool oxide, furfural, hydroxypropanone, linalool and acetic acid. Finally, lemon was shown to be the most divergent of the four fruits, being its aroma profile composed almost exclusively by terpens, namely limonene, γ-terpinene, o-cymene and α-terpinolene. Thirty two volatiles were identified for the first time in the fruit or close related species analysed and 14 volatiles are reported as novel volatile metabolites in fruits. This includes 5 new compounds in kiwi (2-cyclohexene-1,4-dione, furyl hydroxymethyl ketone, 4-hydroxydihydro-2(3H)-furanone, 5-acetoxymethyl-2-furaldehyde and ethanedioic acid), 4 in plum (4-hydroxydihydro-2(3H)-furanone, 5-methyl-2-pyrazinylmethanol, cyclohexylene oxide and 1-methylcyclohexene), 4 in papaya (octaethyleneglycol, 1,2-cyclopentanedione, 3-methyl-1,2-cyclopentanedione and 2-furyl methyl ketone) and 2 in lemon (geranyl farnesate and safranal). It is noteworthy that among the 15 volatile metabolites identified in papaya, 3-methyl-1,2-cyclopentanedione was previously described as a novel PPARγ (peroxisome proliferator-activated receptor γ) agonist, having a potential to minimize inflammation.

VOLATILE COMPOUNDS IN UMBU (SPONDIAS TUBEROSA ARRUDA CÂMARA) FRUITS DURING MATURATION

The determination of aroma compounds in food products is quite complex as most of the volatile compounds responsible for characteristic aroma are present in very small concentrations (mostly in the range of ppm or ppb). However, with the modern instrumental techniques of gas chromatography and mass spectrometry, this objective is being achieved. The umbu fruit is very much appreciated in the north and northeast region of Brazil mainly because of its refreshing and a little acidic flavor. There is no report on changes in volatiles composition during maturation of the fruit. It was therefore the objective of this work to determine the volatiles constituents in half ripe and ripe stages of umbu fruit. The volatile compounds were extracted through a simultaneous solvent distillation and extraction process by using 100 g of pulp of ripe umbu fruit diluted with 100 ml of water which was extracted with 20 ml of n-hexane for 80 min in Likens and Nickerson's apparatus. Volatile compounds were analyzed in a system of high resolution gas chromatograph coupled with mass spectrometer (GC-MS). Identification of volatile components was achieved when the mass spectrum and retention index data of the identified compound matched with that of the authentic standard run under identical conditions. A total of 148 and 159 volatile compounds were detected in half ripe and ripe fruit pulp, respectively. The principal volatile compounds identified in the ripe umbu fruit pulp were limonene, 1-heptanol, 2-pentanol, 3-hexanol, 1-nonanol, 2-octanol; 2-nonanol, 2,2-dimethyl 4-octenal, 3-methylethyl 2-butanoate, butyl benzoate, 3-allyl cyclohexene, 2-acetyl furan, 1-penten-3-one, 3-hexanone, 5-methyl furfural, 2-hexyl furan, β-caryophyllene and methyl-pyrazine.

Reduction screening with endophytic fungi: Synthesis of homochiral secondary alcohols

Twelve strains of endophytic fungi, isolated from various plants (i.e. Eugenia hallii, Schinus molle, Crataegus monogyna, Juniperus communis and Sambucus nigra) sampled in Amazonian forest and in Italy, were screened for their reduction activity with a cocktail of ketones 1–4. The four most active strains [i.e. Phomopsis (FE86 and FE290), Pestalotia and Epicoccum] were chosen for the reduction of 5-hexen-2-one 1, acetophenone 2, cis-bicyclo[3.2.0]hept-2-en-6-one 3, 2-methylcyclohexanone 4, 6-methyl-5-hepten-2-one 5, 2-furyl methyl ketone 6, 1-indanone 7, and 2,4,4-trimethyl-2-cyclohexen-1-one 8 and in all cases the S-alcohols were obtained with variable yields and enantiomeric excesses depending on the strains.

(E)-2-Furyl methyl ketone 2,4-dinitrophenylhydrazone

Crystals of the title compound, C12H10N4O5, were obtained from a condensation reaction of 2,4-dinitro­phenyl­hydrazine and 2-furyl methyl ketone. The mol­ecule displays a nearly planar structure, and the furan ring is slightly twisted by a dihedral angle of 12.62 (6)° with respect to the phenyl­hydrazone plane. The face-to-face separation of 3.287 (7) Å between parallel benzene rings of adjacent mol­ecules indicates the existence of π–π stacking between dinitro­phenyl rings in the crystal structure.