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We report a Pd-catalyzed β-arylation of cyclic α,β-unsaturated O-methyl oximes with aryl iodides. This reaction shows complete regioselectivity and excellent functional group tolerance. β-Arylation of 2-cyclohexen-1-one O-methyl oxime (existing as 2 : 1 E/Z mixture) with certain aryl iodides such as 4-iodoanisole affords only β-arylated (E)-O-methyl oximes.

Aldose reductase (AR) is associated with the onset of diabetic complications. Botryllazine A and its analogues were synthesized and evaluated for human AR inhibitory activity. Analogues possessing aromatic bicyclic systems at the C5 position of the central pyrazine ring exhibited superior AR inhibiting activity relative to the parent botryllazine A. In addition, the benzoyl groups at positions C2 and C3 of the pyrazine ring were dispensable for this improved inhibitory activity. Conversely, a benzoyl group-containing phenolic hydroxyl groups-at either position C2 or C3 of the pyrazine ring was essential for attainment of high inhibitory activity approaching that of sorbinil (a highly effective AR inhibitor).

We report a Pd-catalyzed β-arylation of cyclic α,β-unsaturated O-methyl oximes with aryl iodides. This reaction shows complete regioselectivity and excellent functional group tolerance. β-Arylation of 2-cyclohexen-1-one O-methyl oxime (existing as 2 : 1 E/Z mixture) with certain aryl iodides such as 4-iodoanisole affords only β-arylated (E)-O-methyl oximes.

Utilising CO2 from biogas as a carbon source can introduce energy production systems incorporating microalgae cultivation into wastewater treatment plants (WWTPs). In this study, the effects of utilising membrane-separated CO2 (MSC; CO2 content: 983 ± 11 dm3 m−3)—obtained from biogas using a newly developed separation system—on indigenous microalgae cultivation with treated effluents was investigated. Assuming model cultivation systems, energy balance analysis was conducted to evaluate the feasibility of MSC utilisation and its superiority over flue gas CO2 (FC) from power plants (PPs). Scenarios 1 and 2 used generated biogas of 11.6 and 116 dm3 s−1, and produced MSC (carbon based) were 0.802 and 8.02 g s−1, respectively. Experiments comparing MSC (suspended solids (SS): 166 ± 23 mg dm−3; higher heating value (HHV): 21.1 ± 0.46 kJ g−1) with commercial CO2 (SS: 176 ± 16 mg dm−3; HHV: 21.2 ± 0.90 kJ g−1) revealed no negative effects on microalgae activity, biomass production, or energy content. Energy revenue of the MSC utilisation system was 27.0 MJ per 1 kg injected MSC, which is greater than the energy costs (18.2 and 17.1 MJ kg−1 in scenarios 1 and 2, respectively). MSC utilisation is energetically feasible, and energetically superior to FC utilisation when the PP-to-WWTP distance is over 0.6 and 1.9 km in scenarios 1 and 2, respectively.

We report a 20-year-old male with a past history of diarrhea and discharge of a strobila of a broad tapeworm from his anus 3 months ago. He again noticed passing a tapeworm strobila and he visited our hospital with the tapeworm sample. The macroscopic appearance and the pathological features strongly suggested Diphyllobothriasis. Soon after the first visit to our hospital, a capsule endoscopy was performed with the result of no evidence of strobilae or scoleces. Praziquantel at 20 mg/kg was orally administered once. Before drug administration, egg-like structures were present in the stool. They disappeared soon after drug administration. In human Diphyllobothriasis, Dibothriocephalus nihonkaiensis (D. nihonkaiensis) infection and Dibothriocephalus latus (D. latus) infection are common. These two species are morphologically similar but genetically distinct. Accordingly, polymerase chain reaction (PCR) using genomic DNA of the tapeworm infecting our case was performed for amplifying mitochondrial cytochrome c oxidase subunit 1 (cox1) gene. The amplified DNA fragment by PCR of our case was phylogenetically compared with other mitochondrial cox1 gene sequences of D. nihonkaiensis, D. latus, D. dendriticus, Taenia saginata, Taenia solium and Spirometra erinaceieuropaei. As a result, the tapeworm of our case was most likely within the spectrum of D. nihonkaiensis. Although human diphyllobothriasis is not a life-threatening disease for human beings, it has become a re-emerging problem even in the most developed countries with the increasing popularity of eating raw fish. The knowledge of how to cook or freeze raw fish before eating can reduce the risk of infection. However, without general awareness of human parasite infection, food-borne infections will continue to be a public health problem. Keywords: Tapeworm, Dibothriocephalus nihonkaiensis, Dibothriocephalus latus, Mitochondrial cytochrome c oxidase subunit 1 gene, Praziquantel

A number of (Z)-4-arylmethylene-1H-imidazol-5(4H)-ones, which are related to the fluorescent chromophore of the Aequorea green fluorescent protein (GFP), have been synthesized and evaluated their in vitro inhibitory activity against recombinant human aldose reductase for the first time. The GFP chromophore model 1a, with a p-hydroxy group on the 4-benzylidene and a carboxymethyl group on the N1 position, exhibited strong bioactivity with an IC50 value of 0.36 μM. This efficacy is higher than that of sorbinil, a known highly potent aldose reductase inhibitor. Compound 1h, the 2-naphtylmethylidene analogue of 1a, exhibited the best inhibitory effect among the tested copounds with an IC50 value of 0.10 μM. Structure-activity relationship studies combined with docking simulations revealed the interaction mode of the newly synthesized inhibitors toward the target protein as well as the structural features required to gain a high inhibitory activity. In conclusion, the GFP chromophore model compounds synthesized in this study have proved to be potential drugs for diabetic complications.

We report a Pd-catalyzed arylation of 1,4-naphthoquinones with aryl iodides. This reaction shows excellent functional group tolerance and high regioselectivity when using nonsymmetric 1,4-naphthoquinone. Furthermore, the resulting 2-aryl-1,4-naphthoquinone could be successfully converted into benzo[b]phenanthridine-7,12-dione through treatment with aqueous ammonia, followed by oxidative cyclization using MnO2.

To reduce the pollution load caused by Combined Sewer Overflow (CSO), which significantly affects the properties of water for public use in the event of rain, effective measures are adopted after the outflow behavior and pollution load are carefully studied. In this research, an area of about 127 ha around the confluence zone located in Nagaoka City, Niigata was targeted, the outflow rate, the water quality of CSO and the amount of rainfall were continuously monitored for 1200 days. The observation was started in June 2004 at two points where chamber has been equipped. As a next step, a simulation model with high reproducibility was designed on the basis of the data obtained by continuous observation using MOUSE. Since the water quality was predicted using the model in the case when it could not be measured, the pollution load of CSO was accurately estimated. It was found that the pollution loads of SS and of BOD for eight months (from April to November) were 50×103 kg and 28×103 kg, respectively. In addition, we found that the pollution load basic units of SS and BOD were 59×103 kg km-2 year-1 and 33×103 kg km-2 year-1, respectively.

リン鉱石は枯渇が懸念される資源である一方，下水汚泥焼却灰はリン鉱石と同程度リンを含有し，リン鉱石と代替できる可能性を有する。そこで本研究は，溶融処理を用いたスラグ肥料の作成可能な下水汚泥焼却灰組成範囲と，肥料としての安全性・肥効性の明確化を目的とした。灰組成による影響検討のためモデル灰からスラグ肥料を作製した結果，灰組成中にリン酸17wt%以上，酸化マグネシウム15wt%以上，アルカリ分40wt%以上となる範囲内にすることで品質基準を満たすことを確認した。また実焼却灰でもこの組成範囲に調整することでリン肥料が作製可能なことを確認した。重金属類に対する安全性の検討を行った結果，含有量試験より鉛やクロムなどは肥料取締法基準値を満たすことを確認した。またスラグ肥料を施肥して栽培した作物を分析した結果，植物中の鉛，カドミウム，クロムは食品衛生法の許容上限量を下回り，実土壌への適用が可能であることが示唆された。

膜分離活性汚泥法では高いランニングコストを削減することが課題となっている．高いランニングコストをもたらしている主原因は，膜面付着物を剥離させるために強い曝気が必要なことである．これまでに本研究グループでは膜分離反応槽内に担体を投入することで膜透過性能の向上効果があることを見出しており，担体投入により曝気量が縮減できると考えられた． 本研究では，曝気線速度0.4m/minで担体の無添加系と添加系，曝気線速度0.2m/minで担体を添加系の3条件で，実下水の長期間の連続処理実験を行った．その結果，担体を添加することで，従来より低い曝気線速度でも安定した窒素除去性能および膜透過性能が得られ，薬品洗浄回数も大幅に削減できた．

We measured the mutagen formation potential (MFP) of 42 river water samples from 37 rivers throughout Japan using the Ames mutagenicity assay, to investigate the nationwide level of mutagen precursors contained in river water. The MFP of river water was highest when Salmonella typhimurium strain TA100 was used without metabolic activation. The MFPs ranged from 210 to 20,200 net rev. · l-1 and the median was 2,520 net rev. · l-1, which shows that the values varied greatly between samples. About 60% of the samples showed MFPs in the range from 1,500 to 3,500 net rev. · l-1. Dissolved organic carbon (DOC), E260, NH4-N, NO2-N, NO3-N and T-N concentrations were also measured. A strong positive relationship was observed between logarithmically-transformed DOC and MFP. However, the MFP/DOC ratio varied widely from 110 to 2,160 net rev. · mg-1. We also investigated the relationship between MFP and river basin characteristics such as population density. The results suggest that mutagen precursors are strongly influenced by human activities. In addition, rivers were classified using a cluster analysis of water qualities (MFP, DOC, E260, NH4-N and NO2-N+NO3-N).

In this study, we report a new effective sludge-digestion gas (biogas) adsorption storage technology. The experimental data of the pure and binary adsorption equilibrium of methane and carbon dioxide, which are the main components of the biogas, on five types of activated carbons at a temperature range of 273–333 K and pressures up to 6 MPa, were measured. Pure isotherms were fitted with the Toth and extended Toth models. Binary equilibrium was predicted using the Ideal Adsorbed Solution Theory (IAST) based on the extended Toth model with the experimental data being predicted as well. The differential enthalpy of the pure and binary adsorption was calculated, and storage densities of the binary gases, methane and carbon dioxide, considering the increased activated carbon temperature, were estimated using the adiabat and isobar of mixed gases in the biogas composition.

High-pressure excess adsorption equilibria of methane and carbon dioxide on five microporous activated carbons were measured. Adsorption isotherms were obtained at temperatures ranging from (273 to 333) K and at pressures ranging from (0.5 to 6000) kPa using a static volumetric apparatus. The experimental data were analyzed using the Toth model and the Dubinin−Astakhov model. The isosteric enthalpies of adsorption and the limiting heat of adsorption for both adsorbates on all activated carbons were calculated using the Clausius−Clapeyron equations and the van't Hoff equations, respectively.

都市ごみ焼却灰溶融スラグの有効利用の促進を図るため, 灰組成の違いによるスラグ強度とPb溶出特性の把握を行い, スラグ化に適した灰組成範囲の明確化とpb溶出機構の解明を行った。溶融スラグは, 灰組成を試薬により調整したモデル焼却灰を用い, 1, 400℃で2時間溶融して冷却速度4℃/minの徐冷方法で作成した。スラグを骨材として再利用する際の骨材試験としてすりへり試験を行った結果, 塩基度 (CaO/SiO2) 1.25～1.75の範囲においてGehleniteの結晶が析出し, すりへり減量値が低く, スラグ強度が高くなった。また, 酸性 (pH4) 下の溶出試験では, 塩基度1.0～1.25の範囲にある共晶組成においてPbの溶出率が他の灰組成の2～3倍程度高くなった。さらに, 環告46号法を行った結果, 塩基度1.0～2.0の範囲にある多くの組成において溶出基準を満たすことがわかった。したがって, スラグ化に適した灰組成はスラグの材料強度とPb溶出試験の結果から塩基度1.5～1.75の範囲であると考えられた。さらに, Pbの溶出量は, 同一灰組成ならば, pHを一定とした条件下ではスラグ中のPb含有量に比例することを明らかとした。

一般廃棄物のガス化溶融処理では, 熱分解工程から燃焼・溶融工程までを最適に行うために, 投入する廃棄物をどの程度まで熱分解させるかが重要になってくる。本研究では, 実験試料に模擬ごみを仮定したRDF (廃棄物固形燃料) を用い, 一般廃棄物のガス化溶融処理における熱分解工程の処理条件の違いが, 熱分解残渣, タール, 熱分解ガスの生成に対し, どの程度影響を及ぼすのかを明らかにするとともに, 各熱分解条件で生成した熱分解残渣の熱重量分析および着火温度を測定することで, 燃焼・溶融工程での着火のしやすさを評価した。そして, 燃焼・溶融工程を通して適した熱分解条件を明らかにするために, 各熱分解条件での (1) 熱分解残渣の低位発熱量, (2) 熱分解ガスの低位発熱量, (3) 熱分解残渣の生成割合, (4) 熱分解残渣の燃料比を基に評価を行った。その結果, 熱分解温度450～500℃, 熱分解時間60分程度の条件が適することが明らかになった。

塩基度 (CaO/SiO2) およびAl2O3の量的変動を指標として用い, それらが1) 焼却灰の溶融特性, 2) スラグのすり減り減量, 3) スラグからの金属類の溶出に及ぼす影響について検討した。試料には6成分系の人工灰 (SiO2-CaO-Al2O3-Fe2O3Na2O-P2O5) を用いた。実験から, 1) では塩基度0.54～1.07でOthers (=Al2O3+Fe2O3+Na2O+P2O5) 量15～20mol% (Al2O310mo1%程度) の範囲に低溶融点域の存在することが観察でき, 主要3成分 (SiO2-CaO-Al2O3) の影響が支配的であった。2) ではSi, Al, Ca, Oが複合結晶 (CaAl2Si2O8 (Anorthite) , Ca2Al2SiO7 (Gehlenite) , Ca2SiO4 (Larnite) ) として析出している結晶質スラグであればすり減り減量は30%以下となった。3) ではPb (人工灰にPbOとして0.3mol%添加) の溶出濃度は, 塩基度0.53～3.2, Al2O3量6～15mol%程度の組成で1mg/L以上となった。以上の特性をスパイダーグラフとしてまとめた結果, トレードオフの関係が見られ, 軸スケールを使用目的に応じて限定していくことで適切な組成範囲が把握できると考えられた。

The solvent tetrachloroethylene (PCE), a common soil contaminant, can be completely dechlorinated to ethylene and ethane by microorganisms under anaerobic conditions. Ethylene and ethane are harmless and environmentally acceptable products. This study was conducted to investigate factors influencing on an anaerobic bioremediation of PCE-contaminated soil.An anaerobic enrichment culture, which is capable of dechlorinating PCE completely, sustained its transformation ability in the presence of soil, although the activity was lowered. Addition of the enrichment culture was indispensable for progressing complete dechlorination of PCE in actual contaminated soils. PCE contained in soil was first leached to liquid-phase and then dechlorinated. Therefore, desorbing rate of PCE from soil was an important factor in the bioremediation. PCE was also dechlorinated to ethylene and ethane under the condition of low liquid/solid (L/S) ratio of 0.2l · kg-1 by adding the enrichment culture.

Effect of soluble microbial products (SMP) on permeate flux in a cross-flow type ultrafiltration was investigated.Synthetic wastewater (phenol) was continuously treated by an activated sludge process incorporating membrane solid-liquid separation. Hydraulic retention times and the sludge concentrations of the reactor were kept at 12 hours and 5,000 mg VSS·l-1, respectively. At certain intervals, batch filtration tests using mixed liquor of the reactor were conducted to investigate the mechanism of membrane fouling. The permeate flux dropped gradually, due to increase of SMP concentrations and of fouling mass adhered onto the membrane surface.Batch phenol-degradation reactor and aerobic sludge digestion reactor were operated, and batch filtration tests were conducted to examine which type of SMP has more important role in flux drop. Higher flux drop was observed when the mixed liquor of the sludge digestion reactor was tested at a same level TOC concentrations of SMP. It was found by gel-chromatogram that high-molecular-weight SMP was dominant in the sludge digestion reactor. The results suggest that SMPe (SMP resulted from endogenous cell decomposition) has more significant effect on flux drop.

The two dihydroxylated metabolites of 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline monohydrochloride monohydrate (NIK-247), which is a new drug for the treatment of dementia, were synthesized to determine their chemical structures. Reduction of the tricyclic diketone, 9-amino-2,3,6,7-tetrahydro-1H-cyclopenta[b]quinoline-1,8(5H)-dione, with equivalent molar of NaBH4, afforded the racemic two alcohols, (+/-)-9-amino-2,3,5,6,7,8-hexahydro-8-hydroxy-1H-cyclopenta[b]quinoli n-1-on e and (+/-)-9-amino-2,3,5,6,7,8-hexahydro-1-hydroxy-1H-cyclopenta[b]quinoli n-8- one. (+)-9-Amino-2,3,5,6,7,8-hexahydro-8-hydroxy-1H-cyclopenta[b]quinolin+ ++-1-one was obtained by optical resolution of the corresponding racemic hydroxyketone using (-)-di-p-toluoyl-L-tartaric acid. The optically active dihydroxylated metabolites were obtained by reduction of the (+)-8-hydroxy-1-one with NaBH4.

The two dihydroxylated metabolites of 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline monohydrochloride monohydrate (NIK-247), which is a new drug for the treatment of dementia, were synthesized to determine their chemical structures. Reduction of the tricyclic diketone, 9-amino-2,3,6,7-tetrahydro-1H-cyclopenta[b]quinoline-1,8(5H)-dione, with equivalent molar of NaBH4, afforded the racemic two alcohols, (+/-)-9-amino-2,3,5,6,7,8-hexahydro-8-hydroxy-1H-cyclopenta[b]quinoli n-1-on e and (+/-)-9-amino-2,3,5,6,7,8-hexahydro-1-hydroxy-1H-cyclopenta[b]quinoli n-8- one. (+)-9-Amino-2,3,5,6,7,8-hexahydro-8-hydroxy-1H-cyclopenta[b]quinolin+ ++-1-one was obtained by optical resolution of the corresponding racemic hydroxyketone using (-)-di-p-toluoyl-L-tartaric acid. The optically active dihydroxylated metabolites were obtained by reduction of the (+)-8-hydroxy-1-one with NaBH4.

The C11-C23 segment 4 of swinholide A (1) was synthesized stereoselectively starting from (S)-malic acid via double nitroaldol reaction under high pressure and differentiation of the left and right parts of the symmetric compound 10 as the key steps.

cis-1,2-Dichloroethylene (cis-DCE) is frequently found at significant concentrations in groundwater which is contaminated with tetrachloroethylene or trichloroethylene. Under anaerobic conditions, cis-DCE can be biotransformed via reductive dechlorination to ethylene. Several factors affecting this transformation were investigated using anaerobic sewage sludge as an inoculum. The reductive dechlorination of cis-DCE was observed at 25°C and 15°C but not at 35°C. Supplying a suitable electron donor (organic substrate or hydrogen) was necessary to sustain reductive dechlorination. Glucose, yeast extract, propionate, and hydrogen stimulated dechlorination, while methanol and acetate did not. Anaerobic enrichment cultures capable of dechlorinating cis-DCE to ethylene were developed from the sludge. In the presence of either glucose, yeast extract or propionate (100 mgCOD/l), 0.46 mg/l of cis-DCE was almost completely dechlorinated to ethylene within 4 days by the cultures at 25°C. Transformation rate was somewhat lower in the culture fed with hydrogen. Dechlorinating ability was sustained even in the cultures fed with low concentrations (10 mgCOD/l) of glucose or hydrogen, although the transformation was sometimes insufficient. These results suggest that anaerobic bioremediation processes can be used for removal of chlorinated ethylenes from contaminated groundwater.

The C11-C23 segment 4 of swinholide A (1) was synthesized stereoselectively starting from (S)-malic acid via double nitroaldol reaction under high pressure and differentiation of the left and right parts of the symmetric compound 10 as the key steps.

The inhibitory effect of lipids and prevention of this inhibition in a two-phase anaerobic process were examined using laboratory-scale reactors and batch experiments. Lipids were satisfactorily degraded in a two-phase anaerobic filter while in a single-phase system, inhibition resulted in poor lipid degradation. Unsaturated long-chain fatty acids (LFAs) had a greater inhibitory effect than saturated LFAs. Methane production as well as beta-oxidation (degradation of saturated LFAs) were inhibited by unsaturated LFAs. The saturation of unsaturated LFAs was not inhibited, and palmitate (C16:0) was accumulated in the degradation of oleate (C18:l) or linoleate (C18:2). Greater inhibition was observed at low pH values. Continuous operation of a suspended-growth acidogenic reactor showed that hydraulic retention times (HRTs) of no less than 8 hours were necessary to mitigate the inhibition in a two-phase process. The fact that saturation of oleate occurred at HRTs no less than 8 hours suggests that the saturation of unsaturated LFAs in an acidogenic reactor is essential in the prevention of lipid inhibition in two-phase anaerobic processes.

We studied the interaction of LPS with albumin, hemoglobin or high-density lipoprotein (HDL), and whether the interaction affected the activity of LPS on neutrophils. These proteins disaggregated LPS, depending upon temperature and LPS:protein ratio. Albumin-treated LPS was absorbed by immobilized anti-albumin antibody and was eluted with Triton X-100, indicating that LPS formed a hydrophobic complex with albumin. Rd mutant LPS was not disaggregated by the proteins, and did not form a complex with the proteins. But triethylamine-treated Rd mutant LPS formed complexes. When LPS was incubated with an equal concentration of albumin and with polymyxin B (PMXB), PMXB-LPS-protein three-way complexes were formed. After removal of PMXB, the complexes consisted of 11-15 LPS monomers bound to one albumin or hemoglobin molecule. LPS primed neutrophils for enhanced release of formyl peptide-stimulated superoxide, in a serum- and LPS-binding protein (LBP)-dependent manner. Although LPS plus LBP alone did not prime neutrophils, albumin-, hemoglobin- or HDL-treated LPS primed neutrophils when added with LBP. Triethylamine-treated Rd mutant LPS primed neutrophils only when incubated with one of the proteins and with LBP. Thus, in addition to LBP, disaggregation and complex formation of LPS with one of these proteins is required for LPS to prime neutrophils.

Groundwater replenishment by infiltration of road runoff is expected to be a promising option for ensuring a sustainable urban water cycle. In this study, we performed a soil infiltration column test using artificial road runoff equivalent to approximately 11-12 years of rainfall to evaluate the removal of pollutants by using various chemical analyses and bioassay tests. These results indicated that soil infiltration treatment works effectively to remove most of the pollutants such as organic matter (chemical oxygen demand (CODMn) and dissolved organic carbon (DOC)), P species, polycyclic aromatic hydrocarbons (PAHs), numerous heavy metals and oestrogenic activities. Bioassay tests, including algal growth inhibition test, Microtox and mutagen formation potential (MFP) test, also revealed effective removal of toxicities by the soils. However, limited amounts of NO3, Mn, Ni, alkaline earth metals, perfluorooctane sulphonate (PFOS) and perfluorooctane sulphonamide (FOSA) were removed by the soils and they possibly reach the groundwater and cause contamination.

Tetrachloroethylene (PCE) is one of the most common groundwater contaminants in Japan. PCE can be completely dechlorinated to ethylene (ETY) and ethane (ETA) by anaerobic microorganisms in the presence of a suitable electron donor. This study was conducted to examine the feasibility of using an anaerobic filter for the degradation of PCE in a bioremediation process. Laboratory-scale anaerobic filters were operated at 25°C using ethanol as the electron donor. Rapid start-up of the reactors was achieved by using anaerobic completely PCE-dechlorinating enrichment cultures as the inoculum. During the continuous operating periods, low concentrations (2.8 mg/L) of PCE were almost completely dechlorinated to ETY and ETA at hydraulic retention times of 49-15 hours with 100 mgCOD/L of ethanol. PCE concentrations as high as 80 mg/L was dechlorinated to ETY with a relatively low supply (200 mgCOD/L) of ethanol. Results of this study suggest that the anaerobic filter system is a feasible bioremediation process for the cleanup of groundwater which is contaminated by chlorinated ethylenes.

Acid treatment of o-quinol acetates (2a and 2b) derived from 5-hydroxy-1-benzyltetrahydroisoquinolines (3a and 3b) gave the corresponding 3-hydroxyaporphines (4a and 4b) in high yield.Similarly, the 3-hydroxyhomoaporphines (4c, 4d, and 4e) were excusively synthesized from the corresponding 1-phenethyl o-quinol acetates (2c, 2d, and 2e). On the other hand, no C-noraporphine was formed from the 1-aryl o-quinol acetate (2f); instead, the p-quinone (11) was generated.