2-Naphthaldehyde (β-Naphthaldehyde) by Asch

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PubChem

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Reactions (187)

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Substances (1)

Citations (319)

Conditions

References

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Rx-ID: 268223 Find similar reactions

100%

With dimethyl selenoxide in benzene

5 h; Heating;

Syper; Mlochowski

Synthesis, 1984 , vol. NO. 9, p. 747 - 752 Title/Abstract Full Text View citing articles Show Details

100%

With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) in 1,2-dichloro-ethane

T=120°C; P=7500.6 Torr; 9 h;

Tanaka, Hirotaka; Hashimoto, Kentaro; Suzuki, Kyosuke; Kitaichi, Yasunori; Sato, Mitsuo; Ikeno, Taketo; Yamada, Tohru

Bulletin of the Chemical Society of Japan, 2004 , vol. 77, # 10 p. 1905 - 1914 Title/Abstract Full Text View citing articles Show Details

100%

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tert-butyl alcohol

1 h; Reflux;

Van Arman, Scott A.

Tetrahedron Letters, 2009 , vol. 50, # 33 p. 4693 - 4695 Title/Abstract Full Text View citing articles Show Details

99%

With polymeric complex of oxodiperoxochromium(VI) compound and pyrazine (Pyz-CrO5)n in dichloromethane

0.6 h; Ambient temperature;

Tamami, Bahman; Yeganeh, Hamid

Tetrahedron, 1997 , vol. 53, # 23 p. 7889 - 7896 Title/Abstract Full Text View citing articles Show Details

99.9%

With silica-supported Jones reagent in dichloromethane

0.00269444 h;

Wiles, Charlotte; Watts, Paul; Haswell, Stephen J.

Tetrahedron Letters, 2006 , vol. 47, # 30 p. 5261 - 5264 Title/Abstract Full Text View citing articles Show Details

98%

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole

T=25°C; 1 h; Catalytic behavior; chemoselective reaction; Hide Experimental Procedure

Liu, Yangyang; Xie, Aming; Li, Junjian; Xu, Xiao; Dong, Wei; Wang, Boliang

Tetrahedron, 2014 , vol. 70, # 52 p. 9791 - 9796 Title/Abstract Full Text View citing articles Show Details

4:4.1.2. The oxidation of primary alcohols

General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), DMAP (0.15 mmol, 0.075 equiv) and CH3CN (5 ml). The reaction mixture was stirred at 25 °C open to air until the completion of the reaction, as monitored by TLC. After completion, CH3CN was evaporated under vacuum. The residue was then diluted with CH2Cl2 (5 ml) and filtered through a plug of silica gel to afford the desired product. 96%

With Merrifield's resin-bound N-aminoimidazolium chlorochromate in dichloromethane

24 h; Heating;

Linares; Sanchez; Alajarin; Vaquero; Alvarez-Builla

Synthesis, 2001 , # 3 p. 382 - 388 Title/Abstract Full Text View citing articles Show Details

96%

With potassium carbonate; chlorobenzene; CyJohnPhos; bis(dibenzylideneacetone)-palladium(0) in toluene

T=105°C; 6 h;

Guram, Anil S.; Bei, Xiaohong; Turner, Howard W.

Organic Letters, 2003 , vol. 5, # 14 p. 2485 - 2487 Title/Abstract Full Text View citing articles Show Details

96%

With (2-((2,6-diisopropylphenyl)amino)-4-((2,6-diisopropylphenyl)imino)-pent-2-ene) lithium salt; oxygen; gold(I) chloride in toluene

T=90°C; 10 h;

Guan, Bingtao; Xing, Dong; Cai, Guixing; Wan, Xiaobin; Yu, Nan; Fang, Zhao; Yang, Liping; Shi, Zhangjie

Journal of the American Chemical Society, 2005 , vol. 127, # 51 p. 18004 - 18005 Title/Abstract Full Text View citing articles Show Details

96%

With aluminium trichloride; 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate in acetonitrile

1.5 h; Heating;

Hajipour; Bagheri; Ruoho

Russian Journal of Organic Chemistry, 2006 , vol. 42, # 6 p. 844 - 848 Title/Abstract Full Text View citing articles Show Details

96%

With ferric nitrate

T=60°C; 0.5 h;

Namboodiri, Vasudevan V.; Polshettiwar, Vivek; Varma, Rajender S.

Tetrahedron Letters, 2007 , vol. 48, # 50 p. 8839 - 8842 Title/Abstract Full Text View citing articles Show Details

96%

With potassium carbonate; chlorobenzene in toluene

T=105°C; 6 h;

Symyx Technologies, Inc.

Patent: US6350916 B1, 2002 ; Location in patent: Example 3 ; Title/Abstract Full Text Show Details

96%

With Oxonereg;; 3,3'-diiodo-2,2',6,6'-tetramethoxy-4,4'-biphenyldicarboxylic acid in nitromethane

T=30 - 35°C; 16 h;

Seth, Saona; Jhulki, Samik; Moorthy, Jarugu Narasimha

European Journal of Organic Chemistry, 2013 , # 12 p. 2445 - 2452 Title/Abstract Full Text View citing articles Show Details

95%

With 2-iodoxybenzenesulfonic acid; Oxonereg;; cetyltrimethylammonim bromide in water

T=20°C; 2 h; Green chemistry; chemoselective reaction; Hide Experimental Procedure

Liu, Yangyang; Wang, Boliang

Journal of Chemical Research, 2014 , vol. 38, # 7 p. 427 - 431 Title/Abstract Full Text View citing articles Show Details

IBS-catalysed alcohol oxidation in CTAB micelle; general procedure

General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wtpercent CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product. 95%

With sodium hypochlorite; C186H204N12O36; sodium hydrogencarbonate; potassium bromide in dichloromethane; water

T=0 - 15°C; pH=8.6; 1.5 h;

Beejapur, Hazi Ahmad; Campisciano, Vincenzo; Franchi, Paola; Lucarini, Marco; Giacalone, Francesco; Gruttadauria, Michelangelo

ChemCatChem, 2014 , vol. 6, # 8 p. 2419 - 2424 Title/Abstract Full Text View citing articles Show Details

95%

With (diacetoxyiodo)benzene in dichloromethane

T=20°C; 5 h;

Beejapur, Hazi Ahmad; Campisciano, Vincenzo; Giacalone, Francesco; Gruttadauria, Michelangelo

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 1 p. 51 - 58 Title/Abstract Full Text View citing articles Show Details

94%

With di-tert-butyl-diazodicarboxylate; bathophenanthroline; oxygen; caesium carbonate; copper(l) chloride in toluene

T=20°C; P=760.051 Torr; 3 h;

Nishii, Takeshi; Ouchi, Tomomi; Matsuda, Aya; Matsubara, Yuka; Haraguchi, Yuuko; Kawano, Tomomi; Kaku, Hiroto; Horikawa, Mitsuyo; Tsunoda, Tetsuto

Tetrahedron Letters, 2012 , vol. 53, # 44 p. 5880 - 5882,3 Title/Abstract Full Text Show Details

93%

With dipyridinium dichromate; adogen 464; dihydrogen peroxide; sodium carbonate in various solvent(s) Oxidation; 24 h; Heating;

Delaval, Nicolas; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques

Journal of Chemical Research - Part S, 1999 , # 4 p. 286 - 287 Title/Abstract Full Text View citing articles Show Details

93%

Stage #1: With (-N(SO2C8F17)-(biphenyl-2,2'-diyl)-O-)AlCH3 in toluene

T=21°C; 0.5 h; Stage #2: With pivalaldehyde in toluene

T=21°C; Oppenauer oxidation; 1 h; Further stages.;

Ooi, Takashi; Otsuka, Hidehito; Miura, Tomoya; Ichikawa, Hayato; Maruoka, Keiji

Organic Letters, 2002 , vol. 4, # 16 p. 2669 - 2672 Title/Abstract Full Text View citing articles Show Details

93%

With oxygen; potassium carbonate in toluene

T=90°C; P=760.051 Torr; 10 h;

Zhang, Lei; Li, Pinhua; Yang, Jin; Wang, Min; Wang, Lei

ChemPlusChem, 2014 , vol. 79, # 2 p. 217 - 222 Title/Abstract Full Text View citing articles Show Details

92%

With aluminium trichloride; 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate in acetonitrile

2 h; Heating;

Hajipour, Abdol R.; Bagheri, Hamid R.; Ruoho, Arnold E.

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005 , vol. 44, # 3 p. 577 - 580 Title/Abstract Full Text View citing articles Show Details

92%

With nitric acid; phosphorus pentoxide; silica gel

0.0666667 h;

Hajipour, Abdol R.; Guo, Lian-Wang; Ruoho, Arnold E.

Molecular Crystals and Liquid Crystals, 2006 , vol. 456, # 1 p. 85 - 93 Title/Abstract Full Text View citing articles Show Details

92%

With MTPPD

T=20°C; 0.0666667 h; Neat (no solvent); chemoselective reaction;

Hajipour, Abdol R.; Safaei, Somayeh; Ruoho, Arnold E.

Synthetic Communications, 2009 , vol. 39, # 20 p. 3687 - 3692 Title/Abstract Full Text View citing articles Show Details

92%

With ammonium nitrate; hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen in water; acetonitrile

T=60°C; 5 h; Green chemistry;

Prebil, Rok; Stavber, Gaj; Stavber, Stojan

European Journal of Organic Chemistry, 2014 , vol. 2014, # 2 p. 395 - 402 Title/Abstract Full Text View citing articles Show Details

92%

With ammonium nitrate; hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile

T=60°C; Green chemistry; chemoselective reaction;

Prebil, Rok; Stavber, Gaj; Stavber, Stojan

European Journal of Organic Chemistry, 2014 , vol. 2014, # 2 p. 395 - 402 Title/Abstract Full Text Show Details

92%

With dihydrogen peroxide in neat (no solvent) T=50°C; 0.166667 h; Hide Experimental Procedure

Hajipour, Abdol Reza; Karimi, Hirbod; Masti, Amir

Monatshefte fur Chemie, 2016 , vol. 147, # 2 p. 413 - 423 Title/Abstract Full Text View citing articles Show Details

General experimental procedure for the oxidationreaction

General procedure: Substrate (5 mmol) and ZPFe (0.5 mol percent) were added intoa 25 cm3 two-necked flask. It was heated in an oil bath to50 °C and then, 30 percent H2O2 (0.015 mol) was added slowlywith continuous stirring for the specified time. The reactionprogress was monitored by GC. At the end, the reactionmixture was cooled to room temperature and then, thecatalyst was removed from the reaction mixture by centrifuge.After that, the organic layer was separated from theaqueous phase by extraction with n-hexane and dried overanhydrous CaCl2. The identity of reaction products wasconfirmed by FT-IR, GC–MS, and 1H NMR. 91%

With periodic acid; .LAMBDA.-(+)-tris(acetylacetonato)chromium(III) in acetonitrile

T=20°C; 18 h;

Xu, Liang; Trudell, Mark L.

Tetrahedron Letters, 2003 , vol. 44, # 12 p. 2553 - 2555 Title/Abstract Full Text View citing articles Show Details

90%

With dipicolinic acid,; dihydrogen peroxide; trifluoroacetic acid; zinc dibromide in tetrahydrofuran; water

T=20°C; 16 h;

Wu, Xiao-Feng

Chemistry - A European Journal, 2012 , vol. 18, # 29 p. 8912 - 8915 Title/Abstract Full Text View citing articles Show Details

89%

With manganese(IV) oxide; oxygen in toluene

T=110°C; 8 h; Green chemistry; Hide Experimental Procedure

Kamimura, Akio; Komatsu, Hiroyuki; Moriyama, Takaaki; Nozaki, Yuichiro

Tetrahedron, 2013 , vol. 69, # 29 p. 5968 - 5972 Title/Abstract Full Text View citing articles Show Details

3.1. Oxidation of benzhydrol 1a in the presence of substoichiometric amounts of activated MnO2: preparation of benzophenone 2 (Table 1, entry 6). General procedure#10;

General procedure: Benzhydrol 1 (0.3831 g, 2.08 mmol) was dissolved in toluene (15 mL) and activated MnO2 (purchased from Aldrich, 0.106 g, 1.92 mmol, 50 mg/mmol) was added to the solution. The reaction mixture was heated at 110 °C under oxygen atmosphere for 4 h. Supernatant of the reaction mixture was scooped by pipet. Additional toluene (5 mL) was added to solid residue and washed the solid then the supernatant was scooped by pipet. This washing procedure was repeated for four times. All of toluene solution was combined and concentrated. Crude product was purified by flash chromatography (silica gel/hexane-EtOAc 3:1) to give 2 in 98percent yield (0.373 g, 2.05 mmol). MnO2 residue was examined for the recycling use of the oxidant (Scheme 4, see below).

89%

With tert.-butylhydroperoxide; eosin y in decane; acetonitrile

T=25°C; 32 h; Inert atmosphereIrradiationMolecular sieveGreen chemistry; chemoselective reaction; Hide Experimental Procedure

Devari, Shekaraiah; Rizvi, Masood Ahmad; Shah, Bhahwal Ali

Tetrahedron Letters, 2016 , vol. 57, # 30 p. 3294 - 3297 Title/Abstract Full Text View citing articles Show Details

General procedure for oxidation of alcohols:

General procedure: Oven dried round bottom flask was charged with Eosin Y (5 mmol) alcohol (1 mmol) and 3 equiv. of TBHP (5.5 M in decane) in dry ACN. The resulting mixture was degassed for 15 mins, followed by back filling N2, and then irradiated under Blue LED light (12W, 455 nm) at room temperature (25 oC). After reaction completion monitored through TLC, the mixture was diluted with 15 ml of 10percent NaHCO3 solution, and extracted with EtOAc (3 × 20 ml). The combined organic extracts were washed with brine (20 ml), dried over Na2SO4, and concentrated on vacuo. Purification of the crude product on silica gel using EtOAc:Hexane as solvent system afforded the desired product. 87%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; {[Cu2(1,2-benzenedicarboxylate)2(1,4-bis(1,2,4-triazol-1-ylmethyl)-2,3,5,6-tetrafluorobenzene)2] ·3H2O}n; sodium carbonate in acetonitrile T=75°C; 16 h; Hide Experimental Procedure

Chen, Sheng-Chun; Lu, Sheng-Nan; Tian, Feng; Li, Nan; Qian, Han-Yu; Cui, Ai-Jun; He, Ming-Yang; Chen, Qun

Catalysis Communications, 2017 , vol. 95, p. 6 - 11 Title/Abstract Full Text Show Details

2.2 Catalytic reaction

General procedure: In a typical experiment, 4-methoxybenzyl alcohol (12μL, 0.1mmol), Cu-FMOF (11.3mg, 10mmol percent), TEMPO (7.8mg, 0.05mmol) and NaCO3 (10.6mg, 0.1mmol) in 1mL of air saturated acetonitrile were taken in a 15-mL three-necked round-bottom flask. The solution was magnetically stirred for 16h at 75°C under air atmosphere. The progress of the reaction was monitored via gas chromatography (Shimadzu GC-2010AF) involving a Chromopak capillary column and flame ionization detector. The products were further confirmed by using gas chromatography–mass spectroscopy (GC–MS) (Shimadzu GCMS-2010). The concentrations of 4-methoxybenzyl alcohol and 4-methoxybenzylaldehyde were calibrated by external standard method with standard samples (see Fig. S1). 84%

With iodine; oxygen in ethyl acetate

T=20°C; 24 h; visible light irradiation;

Nakayama, Hiroki; Itoh, Akichika

Chemical and Pharmaceutical Bulletin, 2006 , vol. 54, # 11 p. 1620 - 1621 Title/Abstract Full Text View citing articles Show Details

84%

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione

T=60°C; 3 h;

Moorthy, Jarugu Narasimha; Singhal, Nidhi; Venkatakrishnan

Tetrahedron Letters, 2004 , vol. 45, # 28 p. 5419 - 5424 Title/Abstract Full Text View citing articles Show Details

84%

With Pd(0) nanoparticle supported on aminopropyl grafted silica-based mesocellular foam; air in para-xylene

T=110°C; P=760.051 Torr; 5 h;

Johnston, Eric V.; Verho, Oscar; Kaerkaes, Markus D.; Shakeri, Mozaffar; Tai, Cheuk-Wai; Palmgren, Pal; Eriksson, Kristofer; Oscarsson, Sven; Baeckvall, Jan-E.

Chemistry - A European Journal, 2012 , vol. 18, # 39 p. 12202 - 12206 Title/Abstract Full Text View citing articles Show Details

83%

With potassium osmate; chloroamine-T in water; tert-butyl alcohol

1 h; chemoselective reaction; Hide Experimental Procedure

Devari, Shekaraiah; Deshidi, Ramesh; Kumar, Manjeet; Kumar, Arvind; Sharma, Simmi; Rizvi, Masood; Kushwaha, Manoj; Gupta, Ajai Prakash; Shah, Bhahwal Ali

Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6407 - 6410 Title/Abstract Full Text View citing articles Show Details

oxidation of allylic and benzylic alcohol

General procedure: Chloramine-T (0.5 equiv) was added to a solution of K2[OsO2 (OH)4] (3 molpercent) in t-BuOH/H2O (1:1) followed by the addition of alcohol (1.0 mmol) and kept on stirring till completion (confirmed by TLC). The reaction was quenched by adding sodium sulphite(Na2SO3) and stirred for 30 min. The mixture after extraction with ethyl acetate (twice), usualworkup and purification over silica gel column using Hexane:EtOAc (95:5) afforded pure products. 82%

With sodium tungstate; dihydrogen peroxide; [Me(n-C8H17)3N]HSO4 in water

T=90°C; 4.5 h;

Sato, Kazuhiko; Takagi, Junko; Aoki, Masao; Noyori, Ryoji

Tetrahedron Letters, 1998 , vol. 39, # 41 p. 7549 - 7552 Title/Abstract Full Text View citing articles Show Details

82%

With dihydrogen peroxide; [Me(n-C8H17)3N]HSO4; sodium tungstate in water

T=90°C; Oxidation; 4.5 h;

Sato, Kazuhiko; Aoki, Masao; Takagi, Junko; Zimmermann, Klaus; Noyori, Ryoji

Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 10 p. 2287 - 2306 Title/Abstract Full Text View citing articles Show Details

81%

Stage #1: With oxalyl dichloride; dimethyl sulfoxide in dichloromethane

T=-78°C; 0.25 h; Stage #2: With triethylamine in dichloromethane

T=20°C;

Olsen, Esben P. K.; Madsen, Robert

Chemistry - A European Journal, 2012 , vol. 18, # 50 p. 16023 - 16029 Title/Abstract Full Text View citing articles Show Details

78%

With C16H13ClIrNO(1-); sodium methylate in toluene 20 h; RefluxInert atmosphere;

Fujita, Ken-Ichi; Yoshida, Tetsuya; Imori, Yoichiro; Yamaguchi, Ryohei

Organic Letters, 2011 , vol. 13, # 9 p. 2278 - 2281 Title/Abstract Full Text View citing articles Show Details

78%

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate; copper(I) bromide in water T=20°C; 12 h; Green chemistry;

Ang, Wei Jie; Chng, Yong Sheng; Lam, Yulin

RSC Advances, 2015 , vol. 5, # 99 p. 81415 - 81428 Title/Abstract Full Text View citing articles Show Details

77%

With hydrogen bromide; oxygen; sodium nitrite in water; acetonitrile

T=80°C; 48 h;

Uyanik, Muhammet; Fukatsu, Ryota; Ishihara, Kazuaki

Chemistry - An Asian Journal, 2010 , vol. 5, # 3 p. 456 - 460 Title/Abstract Full Text View citing articles Show Details

76%

With chromium(VI) oxide; periodic acid in dichloromethane; acetonitrile

T=-78°C; 1 h;

Zhang, Suhong; Xu, Liang; Trudell, Mark L.

Synthesis, 2005 , # 11 art. no. M08704SS, p. 1757 - 1760 Title/Abstract Full Text View citing articles Show Details

70%

With iodine; oxygen in acetonitrile

T=20°C; 6 h; Irradiation;

Farhadi, Saeid; Zabardasti, Abedien; Babazadeh, Zaynab

Tetrahedron Letters, 2006 , vol. 47, # 50 p. 8953 - 8957 Title/Abstract Full Text View citing articles Show Details

67%

With 5-chloro-1-indanone; potassium carbonate in nitrobenzene

T=160°C; 15 h; Inert atmosphereGreen chemistry;

Wang, Hu; Zhang, Jin; Cui, Yu-Ming; Yang, Ke-Fang; Zheng, Zhan-Jiang; Xu, Li-Wen

RSC Advances, 2014 , vol. 4, # 65 p. 34681 - 34686 Title/Abstract Full Text View citing articles Show Details

57%

With ammonium chloride in 1,3,5-trimethyl-benzene

T=140°C; P=4560.31 Torr; 3 h;

Yamaguchi, Kazuya; He, Jinling; Oishi, Takamichi; Mizuno, Noritaka

Chemistry - A European Journal, 2010 , vol. 16, # 24 p. 7199 - 7207 Title/Abstract Full Text View citing articles Show Details

51%

With indium isopropoxide; pivalaldehyde in chloroform

T=20°C; Oppenauer Oxidation; 3 h; GloveboxSealed tubeInert atmosphere; Hide Experimental Procedure

Ogiwara, Yohei; Ono, Yuji; Sakai, Norio

Synthesis (Germany), 2016 , vol. 48, # 23 art. no. SS-2016-F0462-OP, p. 4143 - 4148 Title/Abstract Full Text View citing articles Show Details

Oppenauer Oxidation of Alcohols Using In(i-OPr)3; General Procedure

General procedure: To a screw tube in a glovebox was added In(Oi-Pr)3 (29.2 mg, 0.1 mmol). The tube was then sealed and removed from the glovebox, and CHCl3 (1 mL), alcohol (0.5 mmol), and pivalaldehyde (280 μL, 2.5 mmol) were added under N2 in this order. After stirring the mixture at r.t. for 3 h, H2O (1.0 mL) was added to the reaction mixture, which was then extracted with EtOAc. The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (Table 2 and Scheme 2). 50%

94 % Turnov.

With tetrakis(pyridine)silver(II) peroxodisulfate in acetonitrile

3 h; Heating;

Firouzabadi, Habib; Salehi, Peyman; Mohammadpour-Baltork, Iraj

Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 10 p. 2878 - 2880 Title/Abstract Full Text Show Details

With N-chloro-succinimide

Hebbelynck; Martin

Bulletin des Societes Chimiques Belges, 1951 , vol. 60, p. 54,65 Full Text Show Details

With chromic acid

Bamberger; Boekmann

Chemische Berichte, 1887 , vol. 20, p. 1118 Full Text View citing articles Show Details

With dipyridinium dichromate; dihydrogen peroxide; sodium carbonate; adogen 464 in 1,2-dichloro-ethane

T=80°C; 24 h;

Muzart, Jacques; Ajjou, Abdelaziz N'Ait; Ait-Mohand, Samia

Tetrahedron Letters, 1994 , vol. 35, # 13 p. 1989 - 1990 Title/Abstract Full Text View citing articles Show Details

With K10-montmorillonite clay-supported tetrabutylammonium periodate in 2,2,4-trimethylpentane

4 h; Heating; Yield given;

Venkatachalapathy; Rajarajan; Shayira Banu; Pitchumani

Tetrahedron, 1999 , vol. 55, # 13 p. 4071 - 4076 Title/Abstract Full Text View citing articles Show Details

With dinitrogen monoxide; dioxo(tetramesitylporphyrinato)ruthenium(VI) in 1,2-dichloro-ethane

T=120°C; P=7600 Torr; 9 h;

Hashimoto, Kentaro; Kitaichi, Yasunori; Tanaka, Hirotaka; Ikeno, Taketo; Yamada, Tohru

Chemistry Letters, 2001 , # 9 p. 922 - 923 Title/Abstract Full Text View citing articles Show Details

With potassium carbonate; chlorobenzene; CyJohnPhos; bis(dibenzylideneacetone)-palladium(0) in toluene

T=105°C; 6 h;

Bei, Xiaohong; Hagemeyer, Alfred; Volpe, Anthony; Saxton, Robert; Turner, Howard; Guram, Anil S.

Journal of Organic Chemistry, 2004 , vol. 69, # 25 p. 8626 - 8633 Title/Abstract Full Text View citing articles Show Details

Stage #1: With phosphorus pentoxide

T=20°C; 0.00833333 h; Stage #2: With nitric acid

T=20°C; 0.0666667 h;

Hajipour, Abdol R.; Kooshki, Behzad; Ruoho, Arnold E.

Organic Preparations and Procedures International, 2005 , vol. 37, # 6 p. 585 - 589 Title/Abstract Full Text View citing articles Show Details

With Dess-Martin periodane in dichloromethane

T=20°C; 1 h; Inert atmosphere; Hide Experimental Procedure

Moody, Catherine L.; Pugh, David S.; Taylor, Richard J.K.

Tetrahedron Letters, 2011 , vol. 52, # 19 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

Representative experimental procedure: Galactopyranose derivative 24: To 1,2:3,4-di-O-isopropylidene-d-galactopyranose (23) (64 mg, 0.25 mmol) in dry CH2Cl2 (5 mL) at rt under argon was added DMP (209 mg, 0.49 mmol) and the mixture stirred for 1 h. Montmorillonite K10 (50 mg) was then added followed by potassium allyl trifluoroborate (73 mg, 0.49 mmol) and the mixture stirred for 1 h before adding a further portion of DMP (261 mg, 0.62 mmol). After stirring for a further 1 h, the reaction was quenched with sat. aq NaHCO3 (5 mL) and sat. aq Na2S2O3 (5 mL) and allowed to stir for 1 h before diluting with brine (10 mL) and CH2Cl2 (10 mL). The mixture was filtered and then the layers separated. The aqueous portion was further extracted with CH2Cl2 (2 .x. 5 mL) and the combined organic extracts dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (0-5percent acetone in CH2Cl2) to give the compound 24 (55 mg, 75percent) as a colourless micro-crystalline solid, mp 47-49 °C; Rf (CH2Cl2) = 0.15; vmax/cm-1 (thin film) 2988, 2936, 1723 (CO), 1383; [α]D -144 (c 0.4, CH2Cl2); δH (400 MHz, CDCl3) 5.97 (1H, ddt, J = 17.0, 10.5, 7.0, H-8), 5.64 (1H, d, J = 5.0, H-1), 5.20-5.08 (2H, m, H-9), 4.63 (1H, dd, J = 8.0, 2.5, H-3), 4.56 (1H, dd, J = 8.0, 2.0, H-4), 4.35 (1H, dd, J = 5.0, 2.5, H-2), 4.22 (1H, d, J = 2.0, H-5), 3.50 (1H, ddt, J = 18.5, 7.0, 1.5, H-7a), 3.33 (1H, ddt, J = 18.5, 7.0, 1.5, H-7b), 1.49 (3H, s), 1.44 (3H, s), 1.33 (3H, s), 1.30 (3H, s); δC (100 MHz, CDCl3) 207.2 (C-6), 130.0 (C-8), 118.7 (C-9), 109.6, 109.0, 96.4 (C-1), 73.5 (C-5), 72.3 (C-4), 70.6 (C-3), 70.4 (C-2), 44.6 (C-7), 25.9, 25.8, 24.8, 24.2; m/z (ESI) 321 [M+Na]+; [HRMS (ESI): Calcd for C15H22NaO6, 321.1309. Found: [M+Na]+, 321.1317 (-2.7 ppm error)]; [C15H22O6 requires C, 60.39; H, 7.43. Found C, 60.35; H, 7.35]. > 99 %Chromat.

With tert.-butylnitrite; oxygen in acetic acid

T=40°C; 3.5 h; chemoselective reaction;

Karimi, Babak; Badreh, Ebrahim

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 11 p. 4194 - 4198 Title/Abstract Full Text View citing articles Show Details

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide

T=20°C; Hide Experimental Procedure

Moorthy, Jarugu Narasimha; Neogi, Ishita

Tetrahedron Letters, 2011 , vol. 52, # 30 p. 3868 - 3871 Title/Abstract Full Text View citing articles Show Details

General procedure for the one-pot conversion of alcohols to benzimidazoles:

In a typical experiment, the primary alcohol (0.5-0.6 mmol) and IBX (1.1 equiv) were stirred in DMSO at ca. 20 °C. Once the oxidation of alcohol to aldehyde was complete, as judged from TLC analysis, o-phenylenediamine (1.1 equiv) was introduced into the reaction mixture and the reaction mixture was allowed to stir at room temperature until the aldehyde disappeared. At the end of the reaction, DMSO was removed under high vacuum, and the residue was treated with 1.0 M NaHCO3 solution until the pH was 8-9. The organic matter was extracted with ethyl acetate. Regular work-up followed by silica-gel column chromatography led to pure benzimidazoles, which were characterized spectroscopically. With 2,2'-azinobis(3-ethylbenzthiazolinesulfonate); copper(ll) sulfate pentahydrate; oxygen; horseradish peroxidase

T=20°C; P=3000.3 Torr; pH=7; 20 h; Microbiological reactionaq. phosphate bufferEnzymatic reaction;

Fuchs, Michael; Schober, Markus; Pfeffer, Jan; Kroutil, Wolfgang; Birner-Gruenberger, Ruth; Faber, Kurt

Advanced Synthesis and Catalysis, 2011 , vol. 353, # 13 p. 2354 - 2358 Title/Abstract Full Text View citing articles Show Details

82 %Spectr.

With oxygen; sodium carbonate in water

T=100°C; P=760.051 Torr; 24 h; Green chemistry;

Osako, Takao; Uozumi, Yasuhiro

Chemistry Letters, 2009 , vol. 38, # 9 p. 902 - 903 Title/Abstract Full Text View citing articles Show Details

90 %Chromat.

With 2-Acetoxypropene; C16H21ClIrNO in toluene

T=80°C; 10 h; Inert atmosphere; Hide Experimental Procedure

Fujita, Ken-Ichi; Uejima, Takehisa; Yamaguchi, Ryohei

Chemistry Letters, 2013 , vol. 42, # 12 p. 1496 - 1498 Title/Abstract Full Text View citing articles Show Details

General Procedure for the Hydrogen Transfer Oxidation of Benzylic Primary Alcohols Shown in Table 4

General procedure: Under an atmosphere of argon, catalyst 2e (2.0 molpercent), benzylic primary alcohol (1.0 mmol), isopropenyl acetate (1.0 mmol), and toluene (18 mL) were placed in a flask. The mixture was stirred at 80 °C for 10 h. The conversion of benzylic primary alcohol and the yield of benzaldehyde derivative were determined by GC analysis using biphenyl as an internal standard. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Trametes versicolor laccase; oxygen in acetonitrile

T=20°C; pH=5; 24 h; Enzymatic reaction; Reagent/catalystpH-valueTemperatureSolvent;

Bechi, Beatrice; Herter, Susanne; McKenna, Shane; Riley, Christopher; Leimkühler, Silke; Turner, Nicholas J.; Carnell, Andrew J.

Green Chemistry, 2014 , vol. 16, # 10 p. 4524 - 4529 Title/Abstract Full Text View citing articles Show Details

With [bis(acetoxy)iodo]benzene; tetrabutylammomium bromide in ethyl acetate

T=20°C; 24 h; Reagent/catalyst; Hide Experimental Procedure

Salvo, Anna Maria Pia; Campisciano, Vincenzo; Beejapur, Hazi Ahmad; Giacalone, Francesco; Gruttadauria, Michelangelo

Synlett, 2015 , vol. 26, # 9 p. 1179 - 1184 Title/Abstract Full Text View citing articles Show Details

Oxidation Procedure

General procedure: Alcohol (1 mmol) was added to amixture of BAIB (1.1 mmol) and bromide anions (0.2 mmol) inEtOAc (1.5 mL), and the mixture was stirred at room temperaturefor 24 h. The solvent was removed under reduced pressureand the crude product was checked by 1H NMR spectroscopy. Incase of p-nitrobenzyl alcohol, anisole, and p-chlorobenzylalcohol oxidations, the residue was purified by chromatography[PE to separate iodobenzene and PE–EtOAc (10:1) to separatethe corresponding aldehyde]. With oxygen; potassium carbonate in water

T=80°C; 12 h; Green chemistry;

Zou, Houbing; Wang, Runwei; Dai, Jinyu; Wang, Yu; Wang, Xue; Zhang, Zongtao; Qiu, Shilun

Chemical Communications, 2015 , vol. 51, # 78 p. 14601 - 14604 Title/Abstract Full Text View citing articles Show Details

With water; iodine; oxygen in isopropyl alcohol

22 h; Irradiation; Hide Experimental Procedure

Omura, Ryuji; Fujiya, Akitoshi; Yamaguchi, Eiji; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika

Synthesis (Germany), 2016 , vol. 48, # 22 art. no. SS-2016-F0297-OP, p. 3971 - 3975 Title/Abstract Full Text View citing articles Show Details

[3-(4-Bromophenyl)oxiran-2-yl](phenyl)methanone (3aa);9 Typical Procedure

General procedure: I2 (0.315 mmol, 1.05 equiv) and styrene (0.6 mmol, 2 equiv) wereadded to a solution of 4-bromobenzyl alcohol (0.3 mmol, 1 equiv) andH2O (100 μL) in i-Pr2O (3 mL) in a Pyrex test tube under O2. The mixturewas stirred and externally irradiated with four 22 W fluorescentlamps for 22 h. LiOH·H2O (1.8

mmol, 6 equiv) was then added, and thesolution was stirred for a further 2 h under air. The reaction wasquenched with sat. aq Na2S2O3 and the mixture was extracted withEtOAc. The organic layers were combined, dried (MgSO4), and concentratedin vacuo. The crude residue was purified by column chromatography[silica gel, hexane–EtOAc (5:1)] to give a white solid; yield:61.9 mg (0.20 mmol, 68percent). With potassium carbonate in water

T=40°C; 6 h; Irradiation;

Wang, Xiaohui; Baiyila, Dahu; Li, Xiaotian

RSC Advances, 2016 , vol. 6, # 109 p. 107233 - 107238 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 44765888 Find similar reactions

73%

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With nickel(II) chloride hexahydrate; 2,4,5,6-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene; caesium carbonate; dtbbpy in N,N-dimethyl-formamide

T=20°C; 24 h; Schlenk techniqueInert atmosphereIrradiation;

Huang, He; Li, Xiangmin; Yu, Chenguang; Zhang, Yueteng; Mariano, Patrick S.; Wang, Wei

Angewandte Chemie - International Edition, 2017 , vol. 56, # 6 p. 1500 - 1505 Angew. Chem., 2017 , vol. 129, # 6 p. 1522 - 1527,6 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 44765897 Find similar reactions

91%

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With nickel(II) chloride hexahydrate; 2,4,5,6-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene; caesium carbonate; dtbbpy in N,N-dimethyl-formamide

T=20°C; 0.6 h; Schlenk techniqueInert atmosphereFlow reactor;

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Huang, He; Li, Xiangmin; Yu, Chenguang; Zhang, Yueteng; Mariano, Patrick S.; Wang, Wei

Angewandte Chemie - International Edition, 2017 , vol. 56, # 6 p. 1500 - 1505 Angew. Chem., 2017 , vol. 129, # 6 p. 1522 - 1527,6 Title/Abstract Full Text View citing articles Show Details

Rx-ID: 44765906 Find similar reactions

75%

With nickel(II) chloride hexahydrate; 4,4'-Dimethoxy-2,2'-bipyridin; 2,4,5,6-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene; caesium carbonate in N,N-dimethylformamide

T=20°C; 48 h; Schlenk techniqueInert atmosphereIrradiation; Reagent/catalyst;

Huang, He; Li, Xiangmin; Yu, Chenguang; Zhang, Yueteng; Mariano, Patrick S.; Wang, Wei

Angewandte Chemie - International Edition, 2017 , vol. 56, # 6 p. 1500 - 1505 Angew. Chem., 2017 , vol. 129, # 6 p. 1522 - 1527,6 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 826310 Find similar reactions

91%

With carbon tetrabromide; oxygen in acetonitrile

T=20°C; 2 h; IrradiationGreen chemistry;

Tripathi, Shubhangi; Singh, Sachchida N.; Yadav, Lal Dhar S.

RSC Advances, 2016 , vol. 6, # 18 p. 14547 - 14551 Title/Abstract Full Text View citing articles Show Details

90%

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in monofluorobenzene; dimethyl sulfoxide

T=80°C; 20 h;

Nicolaou; Montagnon; Baran; Zhong

Journal of the American Chemical Society, 2002 , vol. 124, # 10 p. 2245 - 2258 Title/Abstract Full Text View citing articles Show Details

90%

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide

T=80°C; 20 h;

Nicolaou; Baran; Zhong

Journal of the American Chemical Society, 2001 , vol. 123, # 13 p. 3183 - 3185 Title/Abstract Full Text View citing articles Show Details

70%

With tert.-butylhydroperoxide

T=120°C; 5 h; Sealed tubeGreen chemistry;

Zarghani, Monireh; Akhlaghinia, Batool

RSC Advances, 2016 , vol. 6, # 45 p. 38592 - 38601 Title/Abstract Full Text View citing articles Show Details

With lt;Mn3O(OAc)6(OAc)(HOAc)gt;*5H2O; lithium chloride in acetic acid

T=100°C; 2 h;

Futami; Hishino; Kurosawa

Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 11 p. 3567 - 3571 Title/Abstract Full Text View citing articles Show Details

With selenium(IV) oxide

T=200°C;

Ssultanow; Rodionow; Schemjakin

Zhurnal Obshchei Khimii, 1946 , vol. 16, p. 2072,2075 Chem.Abstr., 1948 , p. 881 Full Text View citing articles Show Details

Jensen et al.

Acta Chemica Scandinavica (1947-1973), 1952 , vol. 6, p. 180,186 Full Text Show Details

With 9,10-dicyanoanthracene; oxygen; N,N,N,N-tetraethylammonium tetrafluoroborate in acetonitrile

1 h; Irradiationother solvent; Product distribution;

Yamashita, Toshiaki; Tsurusako, Taiji; Yasuda, Masahide; Shima, Kensuke

Chemistry Letters, 1991 , # 9 p. 1487 - 1490 Title/Abstract Full Text Show Details

Multi-step reaction with 2 steps 1: chlorine / 220 °C / diffuses Licht 2: water / 140 - 150 °C View Scheme

Achmatowicz; Lindenfeld

Roczniki Chemii, 1938 , vol. 18, p. 69,72 Chem. Zentralbl., 1939 , vol. 110, # II p. 389 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: bromine / 230 °C / im Sonnenlicht

Mayer,F.; Sieglitz

Chemische Berichte, 1922 , vol. 55, p. 1854

2: hexamethylenetetramine; alcohol View Scheme

Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: N-Bromosuccinimide / tetrachloromethane / 4 h / 20 - 30 °C / |Irradiation 2: 4-methylmorpholine N-oxide / 14 h / 20 °C / |Reflux View Scheme

Tabata, Masayuki; Moriyama, Katsuhiko; Togo, Hideo

European Journal of Organic Chemistry, 2014 , vol. 2014, # 16 p. 3402 - 3410 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 1984172 Find similar reactions

A: 61% B: 20%

With chlorobis(cyclooctene)-iridium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'- binaphthyl in 1,3,5-trimethyl-benzene

T=164°C; 8 h; Reagent/catalystTemperature;

Olsen, Esben P. K.; Madsen, Robert

Chemistry - A European Journal, 2012 , vol. 18, # 50 p. 16023 - 16029 Title/Abstract Full Text View citing articles Show Details

A: 5% B: 42%

With sodium hydroxide; di(rhodium)tetracarbonyl dichloride; N-benzyl-N,N,N-triethylammonium chloride in benzene

T=55°C; 4 h;

Alper, Howard; Hachem, Khaled; Gambarotta, Sandro

Canadian Journal of Chemistry, 1980 , vol. 58, # 15 p. 1599 - 1601 Title/Abstract Full Text Show Details

A: 5% B: 42%

With sodium hydroxide; di(rhodium)tetracarbonyl dichloride; N-benzyl-N,N,N-triethylammonium chloride in benzene

T=55°C; 4 h;

Alper, Howard; Hachem, Khaled; Gambarotta, Sandro

Canadian Journal of Chemistry, 1980 , vol. 58, # 15 p. 1599 - 1601 Title/Abstract Full Text Show Details

With oxygen in toluene

T=90°C; P=760.051 Torr; 10 h; Reagent/catalystSolventTemperature; Hide Experimental Procedure

Seok, Seunghwan; Hussain, Muhammad Asif; Park, Kyun Joo; Kim, Jung Won; Kim, Do Hyun

Ultrasonics Sonochemistry, 2016 , vol. 28, art. no. 2954, p. 178 - 184 Title/Abstract Full Text View citing articles Show Details

2.3.1 Aerobic alcohol oxidation

The oxidation reaction of alcohol was performed according to the following sequence: PdOSNP (40mg, Pd=3.3molpercent of substrate) with toluene (2mL) and alcohol (0.2mmol) was charged in the glass tube reactor. The mixture was stirred at 1000rpm using magnetic stirrer bar under atmospheric pressure of molecular oxygen at 90°C. The conversion and yield were obtained by taking the sample from a mixture at regular intervals and analyzing them with gas chromatography (GC, Younglin GC-6500) and at the end by GC-mass spectroscopy (GC–MS, JEOL GCMS-BU20) to compare with the standard samples. GC analyses were carried out using a flame ionization detector (FID) equipped with a DB-WAX capillary column. GC–MS were recorded at an ionization voltage of 70eV equipped with a DB-WAX capillary column (internal diameter=0.25mm, length=30m).

Rx-ID: 9085483

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85%

With trichlorophosphate in 1,2-dichloro-ethane

T=40°C; Vilsmeier Haack formylation; 1 h; ultrasound irradiation;

Moazzam Ali, Mir; Sana, Sariah; Tasneem; Rajanna; Saiprakash

Synthetic Communications, 2002 , vol. 32, # 9 p. 1351 - 1356 Title/Abstract Full Text View citing articles Show Details

70%

Stage #1: N,N-dimethyl-formamide With trichlorophosphate in acetonitrile

T=-5°C; 1 h; Stage #2: naphthalene With cobalt(II) nitrate in acetonitrile

T=20°C; Vilsmeier-Haack Formylation; 12 h; Stage #3: With water in acetonitrile

Heating; KineticsMechanismCatalytic behavior; Reagent/catalystTimeSolventTemperature; Hide Experimental Procedure

Rajanna; Ferdose, Aneesa; Rajendar Reddy; Arifuddin; Moazzam Ali

Journal of Solution Chemistry, 2016 , vol. 45, # 3 p. 371 - 394 Title/Abstract Full Text View citing articles Show Details

Materials

General procedure: Solvents such as acetonitrile and dichloroethane were of highest purity HPLC grade.Deionized water was further purified over acid dichromate and alkaline permanganatesolutions before use. All the other chemicals used in this study (organic substrates such ashydrocarbons, phenols, and their substituted compounds) were procured from SigmaAldrich Chemicals (Hyderabad, India) with highest purity (99 percent). A carbonate-freesodium hydroxide stock solution was prepared according to standard procedures and theconcentration was systematically checked by titration against potassium hydrogen phthalate.All the metal nitrates used in the present work were of Analytical Reagent (AR) gradeof 99 percent purity (S.D. Fine Chemicals Ltd., India). Stock solutions of metal nitrates (Cu(II),Co(II), Ni(II) and Cd(II) nitrates) were prepared in acetonitrile solvent and standardized byEDTA titrations according to literature procedures [33].2.2 VH Reagents Flasks containing DMF dissolved in a suitable solvent {generally dichloroethane (DCE), oracetonitrile (ACN)}, along with SOCl2 and POCl3, were cooled and thermally equilibratedfor about 30 min at -5 °C by keeping them in a benzene trough chilled from outside withice and NaCl. Requisite amounts of solvent and amide were transferred into a 100 mL flaskand POCl3 or SOCl2 was added drop wise, at -5 °C, with constant stirring. The resultantreagent mixture was kept aside for about an hour to ensure complete formation of the VHadduct. Its concentration was checked by acid–base titration to the bromocresol green endpoint according to literature reports [9– 14]. 2.3 Kinetic MethodOrganic substrates such as hydrocarbons, phenols, and their substituted derivatives wereused for kinetic studies of VH reactions in ACN and DCE. The thermostat (Toshniwal,India) was adjusted to the desired reaction temperature (with a precision of ±0.1 °C). Twodifferent flasks, one containing known amount of Vilsmeier–Haack reagent (DMF/SOCl2or DMF/POCl3) in a suitable solvent, and the other with the substrate solution, were takenand clamped in the thermostatic bath for about 30 min. The reaction was initiated by adding the requisite amount of substrate solution to the reaction vessel containing the othercontents of the reaction mixture. The entire reaction mixture was stirred until the end of thereaction. A kinetic method was adopted to monitor progress of the VH reaction, which issimilar to that reported in our earlier papers [11–14]. Aliquots of the reaction mixture werewithdrawn into a conical flask, containing considerable (and known) amount of hot distilledwater, at different time intervals. The unreacted VH adduct underwent hydrolysis andgave a mixture of acids (hydrochloric and sulfuric acids for DMF/SOCl2 and hydrochloricand phosphoric acids for DMF/POCl3). The acid content was estimated against standardNaOH solution to the bromocresol green end point. Reproducibility of the results wascrosschecked by conducting kinetic runs three to four times. The results were reproduciblewithin ±3 percent error. 2.4 Product Analysis Under Kinetic ConditionsAfter completing the kinetic study of the reaction, excess (remaining part of the reactionmixture) was refluxed further and left aside overnight. The solution was then poured into icecoldwater with vigorous stirring and kept aside for about 2 h. The resultant solution wasneutralized with sodium hydrogen carbonate. The organic phase was extracted with DCE, dried over MgSO4 and the solvent evaporated. Products of the reaction were isolated andfound to be formyl derivatives of the substrates (Scheme 1) as characterized by 1H-NMR andmass spectra with comparison to authentic samples and found to be satisfactory (Table 1).

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Rx-ID: 10119579 Find similar reactions

98%

With sodium periodate; C53H44As2N2O3Ru in water; ethyl acetate; acetonitrile

T=25°C; 0.5 h;

Manikandan, Thimma Sambamoorthy; Ramesh, Rengan; Semeril, David

RSC Advances, 2016 , vol. 6, # 99 p. 97107 - 97115 Title/Abstract Full Text View citing articles Show Details

88%

With oxygen; palladium diacetate; toluene-4-sulfonic acid in water

T=100°C; P=6080.41 Torr; 24 h; Autoclave;

Wang, Azhong; Jiang, Huanfeng

Journal of Organic Chemistry, 2010 , vol. 75, # 7 p. 2321 - 2326 Title/Abstract Full Text View citing articles Show Details

87%

With sodium periodate in water; ethyl acetate; acetonitrile

T=0°C; 3 h;

Vijay Kumar; Prakash Reddy; Sridhar; Srinivas; Rama Rao

Synlett, 2009 , # 5 p. 739 - 742 Title/Abstract Full Text View citing articles Show Details

76%

With C14H24CuN4(2+)*2Cl(1-); dihydrogen peroxide in acetonitrile T=30°C; pH=8; 1 h;

Mi, Chun; Meng, Xiang-Guang; Liao, Xiao-Hong; Peng, Xiao

RSC Advances, 2015 , vol. 5, # 85 p. 69487 - 69492 Title/Abstract Full Text View citing articles Show Details

57.5%

With ruthenium trichloride; [bis(acetoxy)iodo]benzene in dichloromethane; water

T=30°C; 4 h; Hide Experimental Procedure

Mi, Chun; Li, Lu; Meng, Xiang-Guang; Yang, Ren-Qiang; Liao, Xiao-Hong

Tetrahedron, 2016 , vol. 72, # 42 p. 6705 - 6710 Title/Abstract Full Text View citing articles Show Details

Typical method for isolation of aldehydes and diketone

General procedure: The typical solution containing 1 mmol of substrates, 0.1 mol percent RuCl3 and 3 equiv of PhI(OAc)2, was heated and kept at constant 30°C. After Reaction for a period of time, the mixture was then separated with separatory funnel and the dichloromethane phase was dried over anhydrous Na2SO4, filtered and the solvent removed under vacuum. The crude product was purified via a standard silica gel chromatography using hexanes/ethyl acetate as eluent to give the desired aldehyde and diketone products. The isolated products were characterized by NMR (in CDCl3 with TMS as an internal standard) and ESI-MS. All the reactions were performed at least three times to establish there producibility and reliability. 52%

With tert.-butylhydroperoxide; 2.9-dimethyl-1,10-phenanthroline; gold(I) chloride in water; tert-butyl alcohol

T=90°C; 24 h;

Xing, Dong; Guan, Bingtao; Cai, Guixin; Fang, Zhao; Yang, Liping; Shi, Zhangjie

Organic Letters, 2006 , vol. 8, # 4 p. 693 - 696 Title/Abstract Full Text View citing articles Show Details

42%

With 2,2'-azobis(isobutyronitrile); oxygen in nitromethane

T=60°C; P=760.051 Torr; 5 h; Schlenk technique;

Wang, Guang-Zu; Li, Xing-Long; Dai, Jian-Jun; Xu, Hua-Jian

Journal of Organic Chemistry, 2014 , vol. 79, # 15 p. 7220 - 7225 Title/Abstract Full Text View citing articles Show Details

30%

With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tertbutyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen in 1,2-dichloro-ethane

T=70°C; P=760.051 Torr; 6 h; Green chemistry; chemoselective reaction;

Gonzalez-De-Castro, Angela; Xiao, Jianliang

Journal of the American Chemical Society, 2015 , vol. 137, # 25 p. 8206 - 8218 Title/Abstract Full Text View citing articles Show Details

16%

With oxygen; copper diacetate; palladium dichloride in N,N-dimethyl acetamide

T=140°C; P=760.051 Torr; 48 h;

Liu, Yan-Yun; Song, Ren-Jie; Wu, Cui-Yan; Gong, Lu-Bin; Hu, Ming; Wang, Zhi-Qiang; Xie, Ye-Xiang; Li, Jin-Heng

Advanced Synthesis and Catalysis, 2012 , vol. 354, # 2-3 p. 347 - 353 Title/Abstract Full Text View citing articles Show Details

With [bis(acetoxy)iodo]benzene; [(2,2':6',2'-terpyridine)(Cl)RuII(9-oxidophenalenone)] in dichloromethane

T=24.84°C; 16 h; Hide Experimental Procedure

Das, Amit; Ghosh, Tamal Kanti; Dutta Chowdhury, Abhishek; Mobin, Shaikh M.; Lahiri, Goutam Kumar

Polyhedron, 2013 , vol. 52, p. 1130 - 1137 Title/Abstract Full Text View citing articles Show Details

2.6 General methods for catalytic reaction

General procedure: In a typical reaction, the catalyst (0.01 mmol) and 2 equivalent of PhI(OAc)2 in 3 mL of dichloromethane were placed in a 25 mL Schlenk tube and the mixture was stirred for 10 min. The solution immediately turned to reddish brown. The corresponding alkenes and dodecane (1.5 mmol each) were then added in additional 1 mL of solvent and then stirred at room temperature for 16 h at 298 K (353 K for aliphatic substrates). Then the reaction mixture was filtered through a short silica gel column using dichloromethane as eluent prior to GC analysis. The percent conversion and percent selectivity were determined either by GC against authenticated sample with respect to dodecane as an internal standard or by 1H NMR. With tert.-butylhydroperoxide in acetonitrile

T=70°C; 5 h; Reagent/catalyst;

Ge, Danhua; Wang, Jiaqing; Geng, Hongbo; Lu, Shuanglong; Wang, Dongtao; Li, Xinming; Zhao, Xianli; Cao, Xueqin; Gu, Hongwei

ChemPlusChem, 2015 , vol. 80, # 3 p. 511 - 515 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41724966 Find similar reactions

71%

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With [PdCl2(1,3-bis(diphenylphosphino)propane)]; 1,8-diazabicyclo[5.4.0]undec-7-ene in N,N-dimethyl-formamide

T=100°C; P=7500.75 Torr; 20 h; AutoclaveGreen chemistry;

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Yu, Bo; Yang, Zhenzhen; Zhao, Yanfei; Hao, Leiduan; Zhang, Hongye; Gao, Xiang; Han, Buxing; Liu, Zhimin

Chemistry - A European Journal, 2016 , vol. 22, # 3 p. 1097 - 1102 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 42304121 Find similar reactions

88%

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Stage #1: With palladium diacetate; acetic anhydride; PCy3 in N,N-dimethyl-formamide

T=30°C; 1 h; Inert atmosphereGreen chemistry; Stage #2: With triethylamine in N,N-dimethyl-formamide

T=80°C; 6 h; Inert atmosphereGreen chemistry;

Qi, Xinxin; Li, Chong-Liang; Wu, Xiao-Feng

Chemistry - A European Journal, 2016 , vol. 22, # 17 p. 5835 - 5838 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 42387123 Find similar reactions

A: 65%

With iron(III) chloride; copper acetylacetonate; oxygen; N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane

T=90°C; 24 h; Sealed tube; chemoselective reaction;

Zhou, Yao; Rao, Changqing; Mai, Shaoyu; Song, Qiuling

Journal of Organic Chemistry, 2016 , vol. 81, # 5 p. 2027 - 2034 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 42387124 Find similar reactions

A: 63%

With iron(III) chloride; copper acetylacetonate; oxygen; N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane

T=90°C; 24 h; Sealed tube; chemoselective reaction;

Zhou, Yao; Rao, Changqing; Mai, Shaoyu; Song, Qiuling

Journal of Organic Chemistry, 2016 , vol. 81, # 5 p. 2027 - 2034 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 43014803 Find similar reactions

A: 51% B: 12%

With periodic acid; pyridinium chlorochromate in acetonitrile

T=0 - 20°C; 2 h; stereoselective reaction; Hide Experimental Procedure

Killoran, Patrick M.; Rossington, Steven B.; Wilkinson, James A.; Hadfield, John A.

Tetrahedron Letters, 2016 , vol. 57, # 35 p. 3954 - 3957 Title/Abstract Full Text View citing articles Show Details

General procedure 2 – conversion of allyl alcohols to Enals

General procedure: To MeCN (30 mL) was added H5IO6 (5 mmol, 1 eq.) and after 10 min of vigorous stirring, the temperature was lowered to 0 °C. Allyl alcohol (5 mmol, 1 eq.) was added followed by the dropwise addition of PCC (5 molpercent) in MeCN (0.5 mL). The reaction mixture was stirred at room temperature for 2 h and then diluted with EtOAc (50 mL), washed with water (50 mL), saturated aq. Na2SO4 (2 x 50 mL) and dried over Mg2SO4. The crude product was purified by silica flash chromatography (hexane : EtOAc, 8:2).

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Rx-ID: 43932028 Find similar reactions

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Hyodo, Kengo; Togashi, Kosuke; Oishi, Naoki; Hasegawa, Genna; Uchida, Kingo

Green Chemistry, 2016 , vol. 18, # 21 p. 5788 - 5793 Title/Abstract Full Text View citing articles Show Details

With perchloric acid in dichloromethane-d2; water

T=23°C; 24 h; Inert atmosphere;

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Rx-ID: 43932063 Find similar reactions

With perchloric acid in dichloromethane-d2; water

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Hyodo, Kengo; Togashi, Kosuke; Oishi, Naoki; Hasegawa, Genna; Uchida, Kingo

T=23°C; 24 h; Inert atmosphere;

Green Chemistry, 2016 , vol. 18, # 21 p. 5788 - 5793 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 44075120 Find similar reactions

A: 96 %Spectr. B: 6 %Spectr.

Stage #1: With 2-fluoropyridine; trifluoromethylsulfonic anhydride in dichloromethane

T=0°C; 0.333333 h; Inert atmosphere; Stage #2: With 1,1,3,3-Tetramethyldisiloxane in dichloromethane

T=0 - 20°C; 6.16667 h; Inert atmosphere; Hide Experimental Procedure

Lang, Qi-Wei; Hu, Xiu-Ning; Huang, Pei-Qiang

Science China Chemistry, 2016 , vol. 59, # 12 p. 1638 - 1644 Title/Abstract Full Text View citing articles Show Details

2.1.1 General procedure for reduction of secondary amidesto aldimines (general procedure A)

General procedure: Into a solution of an amide (1.0 mmol) in 4 mL of anhydrous dichloromethane was added 2-fluoropyridine (117mg,103 μL, 1.2 mmol). After being cooled to 0 °C, trifluoromethanesulfonicanhydride (Tf2O) (310 mg, 185 μL, 1.1mmol) was added dropwise via a syringe and the mixturewas stirred for 20 min. To the resulting mixture, 1,1,3,3-tetramethyldisiloxane (TMDS) (94 mg, 124 μL, 0.7 mmol)was added dropwise and the resulting mixture was stirredfor 10 min at 0 °C. The mixture was allowed warming up toroom temperature and stirred for 6 h.Quenching with NaHCO3 (sat.): the reaction wasquenched by addition of 0.5 mL of a saturated aqueous solutionof sodium bicarbonate (NaHCO3) and diluted with 30mL of dichloromethane. Then 1,3,5-trimethoxybenzene(168.2 mg, 1.0 mmol) was added as internal standard. Thebiphasic mixture was transferred to a separation funnel andthe layers were separated. The aqueous layer was extractedwith dichloromethane (5 mL×2). The combined organiclayers were dried over anhydrous sodium sulphate(Na2SO4), filtered, and concentrated under reduced pressure.Yields of crude imines were calculated by integration of 1HNMR spectra.Quenching with NaH: the solvent was removed through adrying tube charged with anhydrous CaCl2 under reducedpressure, then 4 mL of THF and NaH (60 mg, 2.5 mmol,60percent dispersion on mineral oil) were added. The resultingsuspension was stirred at r.t. for 20 min. Then 1,3,5-trimethoxybenzene (168.2 mg, 1.0 mmol) was added asinternal standard. Yields of crude imines were calculated byintegration of 1H NMR spectra. A

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With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; C18H17N2O2P in tetrahydrofuran

T=170°C; 24 h; Inert atmosphereSchlenk technique;

Sahoo; Jiang; Bruneau; Sharma; Suresh; Achard

RSC Advances, 2016 , vol. 6, # 102 p. 100554 - 100558 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 760289 Find similar reactions

98%

With dipotassium hydrogenphosphate; dimethyl selenoxide in 1,2-dichloro-ethane

6 h; Heating;

Syper; Mlochowski

Synthesis, 1984 , vol. NO. 9, p. 747 - 752 Title/Abstract Full Text View citing articles Show Details

95%

With pyridine N-oxide; silver(l) oxide in acetonitrile

T=25°C;

Chen, David X.; Ho, Chi M.; Rudy Wu; Wu, Peter R.; Wong, Freeman M.; Wu, Weiming

Tetrahedron Letters, 2008 , vol. 49, # 26 p. 4147 - 4148 Title/Abstract Full Text View citing articles Show Details

94%

With hexamethylenetetraamine; water; sodium dodecyl-sulfate; lanthanum(lll) triflate

T=100°C; Sommelet Aldehyde Synthesis; 1.5 h; Green chemistry; Hide Experimental Procedure

Xu, Wenhao; Su, Weike

2014 , vol. 38, # 12 art. no. A3, p. 710 - 714 Title/Abstract Full Text View citing articles Show Details

Synthesis of 3o; typical procedure

General procedure: Hexamethylenetetramine 1 (70.1 mg), SDS (3.4 mg) and lanthanum triflate (17.6 mg) were dissolved in water (0.5 mL). Then 1o (271 mg) was added to the flask. The mixture was refluxed for 4 h to complete the reaction, which was monitored by TLC. The reaction mixture was extracted with EtOAc three times and the combined organic phases were distilled under reduced pressure. The crude product was purifiedby column chromatography on silica gel using hexane: EtOAc (5 : 1) as eluent to give 3o, recrystallisation of which from EtOH gave white crystals, 147 mg (71percent) (Table 3, entry 1).

87%

With potassium nitrite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen in water

3 h; Reflux;

Liu, Qifa; Lu, Ming; Yang, Fei; Wei, Wei; Sun, Feng; Yang, Zhenbang; Huang, Sufeng

Synthetic Communications, 2010 , vol. 40, # 8 p. 1106 - 1114 Title/Abstract Full Text View citing articles Show Details

85%

With sodium nitrate; acetic acid in water

3 h; Reflux;

Hu, Yu Lin; Wei, Wei; Liu, Qi Fa; Lu, Ming

Bulletin of the Chemical Society of Ethiopia, 2010 , vol. 24, # 2 p. 277 - 282 Title/Abstract Full Text View citing articles Show Details

85%

With sodium periodate in dichloromethane

T=40 - 50°C; Ionic liquid;

Hullio, Ahmed Ali; Mastoi; Khan, Khalid

Asian Journal of Chemistry, 2011 , vol. 23, # 12 p. 5411 - 5418 Title/Abstract Full Text View citing articles Show Details

83%

With dihydrogen peroxide in ethanol

3 h; Heating;

Tang, Jingting; Zhu, Jinlong; Shen, Zongxuan; Zhang, Yawen

Tetrahedron Letters, 2007 , vol. 48, # 11 p. 1919 - 1921 Title/Abstract Full Text View citing articles Show Details

82%

With sodium periodate in N,N-dimethyl-formamide

T=150°C; 0.583333 h;

Das, Sasmita; Panigrahi; Maikap, Golak C.

Tetrahedron Letters, 2003 , vol. 44, # 7 p. 1375 - 1377 Title/Abstract Full Text View citing articles Show Details

66%

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide

T=65°C; 5 h;

Moorthy, Jarugu Narasimha; Singhal, Nidhi; Senapati, Kalyan

Tetrahedron Letters, 2006 , vol. 47, # 11 p. 1757 - 1761 Title/Abstract Full Text View citing articles Show Details

30%

With pyridine N-oxide

0.0333333 h; Irradiationwith microwave irradiation;

Barbry, Didier; Champagne, Philippe

Tetrahedron Letters, 1996 , vol. 37, # 43 p. 7725 - 7726 Title/Abstract Full Text View citing articles Show Details

With hexamethylenetetraamine; acetic acid

Badger

Journal of the Chemical Society, 1941 , p. 535,537 Full Text View citing articles Show Details

With ethanol; hexamethylenetetraamine

Mayer,F.; Sieglitz

Chemische Berichte, 1922 , vol. 55, p. 1854 Full Text View citing articles Show Details

With 2-nitropropane; sodium methylate in methanol

T=20 - 40°C; 7 h;

Hashizume; Ito; Yamada; Nagashima; Kanao; Tomoda; Sunazuka; Kumagai; Omura

Chemical and pharmaceutical bulletin, 1994 , vol. 42, # 3 p. 512 - 520 Title/Abstract Full Text View citing articles Show Details

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in dimethyl sulfoxide

T=60°C; Hide Experimental Procedure

Moorthy, Jarugu Narasimha; Neogi, Ishita

Tetrahedron Letters, 2011 , vol. 52, # 30 p. 3868 - 3871 Title/Abstract Full Text View citing articles Show Details

General procedure for preparation of benzimidazoles from corresponding benzyl bromides.

In a typical procedure, 1.0 equiv of benzyl bromide, 1.1-1.5 equiv IBX (depending upon the substrates) were dissolved in 2.0 mL of dry DMSO, and the reaction mixture was stirred at 60 °C. The progress of the reaction was monitored by TLC analysis. When benzyl bromide was found to be completely converted to benzaldehyde, 1.1-1.5 equiv of o-phenylenediamine was added after cooling the reaction mixture to room temperature. After completion of the reaction as monitored by TLC analysis, the reaction mixture was quenched with water. The solvent DMSO was distilled off in vacuo, and the organic matter was extracted with ethyl acetate. The combined extract was treated with NaHCO3 to remove the iodo acid formed during the reaction followed by brine. The solvent was removed in vacuo and the residue was subjected to silica gel-chromatography to isolate the product, which was characterized by NMR analyses. 237.4 mg

With 4-methylmorpholine N-oxide

T=20°C; 14 h; Reflux;

Tabata, Masayuki; Moriyama, Katsuhiko; Togo, Hideo

European Journal of Organic Chemistry, 2014 , vol. 2014, # 16 p. 3402 - 3410 Title/Abstract Full Text View citing articles Show Details

With sodium hydrogencarbonate; dimethyl sulfoxide

T=90°C; Kornblum Aldehyd Synthesis; 3 h; Hide Experimental Procedure

Adib, Mehdi; Sheikhi, Ehsan; Azimzadeh, Marjan

Tetrahedron Letters, 2015 , vol. 56, # 15 art. no. 45870, p. 1933 - 1936 Title/Abstract Full Text View citing articles Show Details

General procedure for the preparation of compounds 4a–p:

General procedure: A mixture of theappropriate benzylic substrate (1 mmol) and NaHCO3 (0.092 g, 1.1 mmol) inDMSO (0.75 mL) was stirred for 3 h at 90 C. Next, the appropriate carboxylicacid (1.2 mmol) and isocyanide (1.2 mmol) were added to the mixture andstirring was continued at 90 C for 2 h. After completion of the reaction, themixture was cooled to ambient temperature. Next, H2O (2 mL) was added tothe mixture and stirring was continued for 15 min at ambient temperature.The resulting precipitate was filtered, washed with H2O, dried, andrecrystallized from n-hexane/EtOAc (3:1) to afford the pure product 4. [a-Acyloxyamide 4a was purified by column chromatography using n-hexane-EtOAc (4:1) as eluent].v

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89%

With N,N,N',N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite in toluene

T=100°C; P=3750.38 Torr; 20 h; Inert atmosphere;

Neumann, Helfried; Kadyrov, Renat; Wu, Xiao-Feng; Beller, Matthias

Chemistry - An Asian Journal, 2012 , vol. 7, # 10 p. 2213 - 2216 Title/Abstract Full Text View citing articles Show Details

79%

With N,N,N',N,-tetramethylethylenediamine; hydrogen; palladium diacetate; di-(1-adamantyl)-n-butylphosphine in toluene

T=80°C; P=1200.12 Torr; 40 h; Inert atmosphere; Pressure;

Christensen, Stig Holden; Olsen, Esben P. K.; Rosenbaum, Jascha; Madsen, Robert

Organic and Biomolecular Chemistry, 2015 , vol. 13, # 3 p. 938 - 945 Title/Abstract Full Text View citing articles Show Details

92 % Chromat.

With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; di-(1-adamantyl)-n-butylphosphine; palladium diacetate in toluene

T=100°C; P=3750.3 Torr; 16 h;

Klaus, Stefan; Neumann, Helfried; Zapf, Alexander; Struebing, Dirk; Huebner, Sandra; Almena, Juan; Riermeier, Thomas; Gross, Peter; Sarich, Martin; Krahnert, Wolf-Ruediger; Rossen, Kai; Beller, Matthias

Angewandte Chemie - International Edition, 2006 , vol. 45, # 1 p. 154 - 158 Title/Abstract Full Text View citing articles Show Details

92 % Chromat.

With N,N,N',N,-tetramethylethylenediamine; hydrogen; di-(1-adamantyl)-n-butylphosphine; palladium diacetate in toluene

T=100°C; P=3750.38 Torr; 16 h;

Brennfuehrer, Anne; Neumann, Helfried; Klaus, Stefan; Riermeier, Thomas; Almena, Juan; Beller, Matthias

Tetrahedron, 2007 , vol. 63, # 27 p. 6252 - 6258 Title/Abstract Full Text View citing articles Show Details

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With LDBMOA in tetrahydrofuran; hexane

T=0°C; 0.5 h; Hide Experimental Procedure

Kim, Yu Ri; An, Duk Keun

Bulletin of the Korean Chemical Society, 2012 , vol. 33, # 12 p. 4194 - 4196 Title/Abstract Full Text View citing articles Show Details

Partial Reduction of Tertiary Amides and AromaticNitriles to Aldehydes with LDBMOA.

General procedure: The following procedure for reduction of N,N-dimethylbenzamide with LDBMOA is representative. To a solution of N,N-dimethylbenzamide (0.149 g, 1.0 mmol) in THF (10.0 mL) containing naphthalene as an internal standard was added LDBMOA (2.4 mL, 0.5 M in THF-hexanes, 1.2 mmol) at 0 °C. After 30 min, the reaction mixture was hydrolyzed with 1 N aq HCl (10 mL) and extracted with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate, and filtered. After the removal of solvents in vacuum and purification of residue by column chromatography on silica gel gave benzaldehyde (0.103 g, 97percent). > 99 %Chromat.

Shin, Won Kyu; Jang, Hee Mang; Choi, Byung Hoon; Yoo, Jaeduk; An, Duk Keun

Bulletin of the Korean Chemical Society, 2015 , vol. 36, # 7 p. 1919 - 1921 Title/Abstract Full Text View citing articles Show Details

With C11H25AlNO4(1-)*Na(1+) in tetrahydrofuran; toluene T=0 - 20°C; 0.5 h; Hide Experimental Procedure

Partial Reduction of Tertiary Amides to CorrespondingAldehydes.

General procedure: The following experimental procedure describes a representative example of the partial reduction of N,N-dimethylbenzamide to benzaldehyde. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum,was charged with N,N-dimethylbenzamide (0.07 mL,0.5 mmol) and THF (5 mL). After cooling to 0 C, piperidine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at room temperature. The reaction was quenched with 1 N aqueous HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The organic layer was dried over anhydrous magnesium sulfate. GC analysis showed quantitative conversion to benzaldehyde. All products listed in Table 2 were confirmed through comparison with the GC data of authentic samples. A

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A: 74 %Chromat. B: 10 %Chromat.

Kumar, Girijesh; Kumar, Gulshan; Gupta, Rajeev

Inorganic Chemistry, 2015 , vol. 54, # 6 p. 2603 - 2615 Title/Abstract Full Text View citing articles Show Details

With tert.-butylhydroperoxide; 2C21H13N3O6(2-)*4Co(2+)*19H2O*HO(1-) in neat (no solvent) T=50°C; 4 h; Green chemistry;

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A: 8% B: 87%

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Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima

RSC Advances, 2015 , vol. 5, # 16 p. 12048 - 12051 Title/Abstract Full Text View citing articles Show Details

With sodium tetrahydroborate; NiCl2·6H2O in methanol

0.25 h; chemoselective reaction;

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A: 7% B: 90%

Khurana, Jitender M.; Dawra, Kiran; Sharma, Purnima

RSC Advances, 2015 , vol. 5, # 16 p. 12048 - 12051 Title/Abstract Full Text View citing articles Show Details

With sodium tetrahydroborate; NiCl2·6H2O in methanol

2 h; chemoselective reaction;

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With LDBBA in tetrahydrofuran; hexane

T=0°C; Inert atmosphere; chemoselective reaction; Hide Experimental Procedure

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Rx-ID: 41774495 Find similar reactions

An, Jae Sung; Shin, Won Kyu; An, Duk Keun

Bulletin of the Korean Chemical Society, 2015 , vol. 36, # 12 p. 2928 - 2931 Title/Abstract Full Text View citing articles Show Details

Partial Reduction of Weinreb Amides to the CorrespondingAldehydes.

General procedure: The following experimental procedure for the partial reduction of N-methoxy-N-methylbenzamide to benzaldehyde is representative. A dry, argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with N-methoxy-N-methylbenzamide (0.08 mL, 0.5 mmol) and THF (5 mL). After cooling to 0° C, LDBBA (1.38 mL, 0.4M 0.55 mmol) was added dropwise and the mixture was stirred for 30 min at the same temperature. The reaction was quenched with 1N aqueous HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The organic layer was dried over anhydrous magnesium sulfate. GC analysis

showed quantitative conversion to benzaldehyde. All products in Table 2 were confirmed through a comparison with the GC data of an authentic sample.

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93%

With oxygen; copper diacetate in dimethyl sulfoxide

T=120°C; 18 h; Sealed tube;

Feng, Qiang; Song, Qiuling

Journal of Organic Chemistry, 2014 , vol. 79, # 4 p. 1867 - 1871 Title/Abstract Full Text View citing articles Show Details

87%

With sodium azide; [bis(acetoxy)iodo]benzene in acetonitrile

T=0 - 20°C; 0.333333 h;

Telvekar, Vikas N.; Sasane, Kulbhushan A.

Synlett, 2010 , # 18 p. 2778 - 2780 Title/Abstract Full Text View citing articles Show Details

70%

With mercury(II) fluoride; oxygen in acetonitrile

T=25°C; 24 h; Irradiation;

Farhadi, Saeid; Zaringhadam, Parisa; Sahamieh, Reza Zarei

Tetrahedron Letters, 2006 , vol. 47, # 12 p. 1965 - 1968 Title/Abstract Full Text View citing articles Show Details

62%

With oxygen; mercury(II) oxide in methanol; acetonitrile

T=25°C; UV-irradiation;

Habibi, Mohammad H.; Farhadi, Saeid

Journal of Chemical Research, 2004 , # 4 p. 296 - 297 Title/Abstract Full Text View citing articles Show Details

50%

With tetrabutylammonium (meta)periodate in 1,4-dioxane

16 h; Heating;

Santaniello, Enzo; Ponti, Federico; Manzocchi, Ada

Tetrahedron Letters, 1980 , vol. 21, p. 2655 - 2656 Title/Abstract Full Text View citing articles Show Details

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100%

With H6P2W18O62 in toluene

T=100°C; 0.0833333 h;

Romanelli; Autino; Baronetti; Thomas

Synthetic Communications, 2004 , vol. 34, # 21 p. 3909 - 3914 Title/Abstract Full Text View citing articles Show Details

95%

With rice husk supported FeCl3 nanoparticles in ethanol

T=70°C; 0.166667 h; Hide Experimental Procedure

Shirini, Farhad; Akbari-Dadamahaleh, Somayeh; Mohammad-Khah, Ali

Journal of Molecular Catalysis A: Chemical, 2012 , vol. 363-364, p. 10 - 17 Title/Abstract Full Text View citing articles Show Details

2.9 General procedure for deprotection of 1,1-diacetates#10;

General procedure: A solution of the substrate (1 mmol) in EtOH (3 mL) was stirred as FeCl3-rice husk (0.08 g) was added. The mixture was stirred and heated at 70 °C. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was filtered to separate the solid catalyst. The combined filtrates were concentrated on a rotary evaporator to remove EtOH. Water (5 mL) was added and the product was extracted with Et2O (3–5 mL). The organic layer was washed with a saturated solution of NaHCO3 and dried over MgSO4. The solvent was evaporated under reduced pressure. The resultant product was passed through a short column of silica gel (n-hexan–EtOAc, 9:1) to afford pure aldehyde. 94%

With ethanol

T=50 - 60°C; 0.166667 h; Hide Experimental Procedure

Khaligh, Nader Ghaffari

Chinese Journal of Catalysis, 2014 , vol. 35, # 3 p. 329 - 334 Title/Abstract Full Text Show Details

2.3. General procedure for the deprotection of 1,1 diacetates

General procedure: A mixture of the 1,1 diacetate of the aldehyde (5 mmol) andP(4 VPH)ClO4 (20 mg) in ethanol (5 mL) was stirred at 50–60°C. Upon completion of the reaction (as determined by TLC),the mixture was filtered to remove the catalyst. The filtrate wascollected and distilled to dryness to give a residue, which waspartitioned between water (10 mL) and Et2O (5 mL). The etherlayer was collected and the aqueous layer was back extractedwith Et2O (2 × 5 mL). The combined ether layers were washedwith a saturated solution of NaHCO3 (5 mL) and dried overanhydrous Na2SO4. The solvent was removed under vacuum togive the crude product as a residue, which was purified by silicagel column chromatography (n hexane:ethyl acetate = 85:15(v/v)) to afford the pure aldehyde.

92%

With cerium(III) chloride; sodium iodide in acetonitrile

2 h; Heating;

Reddy, G. Sudhakar; Radhika; Neelakantan, Parvathi; Iyengar

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002 , vol. 41, # 4 p. 863 - 864 Title/Abstract Full Text View citing articles Show Details

90%

With sulfonated rice husk ash in acetonitrile

T=60°C; 0.0833333 h; Hide Experimental Procedure

Shirini, Farhad; Mamaghani, Manouchehr; Seddighi, Mohadeseh

Catalysis Communications, 2013 , vol. 36, p. 31 - 37 Title/Abstract Full Text View citing articles Show Details

2.5 General procedure for the deprotection of 1,1-diacetates#10;

General procedure: A mixture of 1,1-diacetate (1 mmol), RHA-SO3H (30 mg) in acetonitrile (2 mL) was stirred vigorously at 60 °C. After completion of the reaction (monitored by TLC), the organic solvent was evaporated. Then the reaction mixture was diluted by ethyl acetate (20 mL) and filtered to separate the catalyst. The organic phase was washed with 10percent aqueous solution of sodium bicarbonate (2 × 10 mL) to remove excess of Ac2O and dried over Na2SO4. The solvent was evaporated under reduced pressure. The resultant product was passed through a short column of silica gel (n-hexane-EtOAc, 9:1) to afford the pure aldehyde.#10; 89%

With β-cyclodextrin in methanol; water

T=60°C; 7 h; Product distribution;

Arjun Reddy; Rajender Reddy; Bhanumathi; Rama Rao

Synthetic Communications, 2002 , vol. 32, # 2 p. 273 - 277 Title/Abstract Full Text View citing articles Show Details

88%

With carbon tetrabromide in acetonitrile

6 h; Heating;

Ramalingam; Srinivas; Subba Reddy; Yadav

Synthetic Communications, 2001 , vol. 31, # 7 p. 1091 - 1095 Title/Abstract Full Text View citing articles Show Details

85%

With SaSA

T=90°C; 0.1 h; Neat (no solvent);

Shirini; Mamaghani; Mostashari-Rad; Abedini

Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 8 p. 2399 - 2401 Title/Abstract Full Text View citing articles Show Details

With indium(III) chloride in water

T=20°C;

Yadav; Subba Reddy; Srinivas, Ch.

Synthetic Communications, 2002 , vol. 32, # 8 p. 1175 - 1180 Title/Abstract Full Text View citing articles Show Details

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With naphthalene in tetrahydrofuran; hexane

T=0°C; 3 h;

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Kim, Min Sung; Choi, Young Mi; An, Duk Keun

Tetrahedron Letters, 2007 , vol. 48, # 29 p. 5061 - 5064 Title/Abstract Full Text View citing articles Show Details

89 % Chromat.

With sodium diisobutyl(t-butoxy)aluminum hydride in tetrahydrofuran; hexane

T=0°C; 1 h;

Song, Jung In; An, Duk Keun

Chemistry Letters, 2007 , vol. 36, # 7 p. 886 - 887 Title/Abstract Full Text View citing articles Show Details

> 99 %Chromat.

Stage #1: With morpholine; diisobutylaluminium hydride in tetrahydrofuran; hexane

T=0°C; 3.16667 h; Inert atmosphere; Stage #2: With diisobutylaluminium hydride in tetrahydrofuran; hexane

T=0°C; 0.166667 h; Inert atmosphere; Hide Experimental Procedure

Jeon, Ah Ram; Kim, Min Eai; Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun

Tetrahedron, 2014 , vol. 70, # 29 p. 4420 - 4424 Title/Abstract Full Text View citing articles Show Details

4.4 Partial reduction of aromatic esters to corresponding aldehydes (Table 4)

General procedure: The following experimental procedure for the partial reduction of ethyl benzoate to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.18mL, 2.1mmol) and THF (10mL). After cooling to 0°C, DIBALH (2.0mL, 1.0M in hexane, 2.0mmol) was added dropwise and the mixture was stirred for 3h at the same temperature. Ethyl benzoate (0.14g, 1.0mmol) was added slowly to the reaction mixture, which was stirred for 10min. Then, DIBALH (1.1mL, 1.0M in hexane, 1.1mmol) was added and the mixture was stirred for 10min again. The reaction was stopped aqueous 1N HCl (10mL) and extracted with diethyl ether (2×10mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by short column chromatography on silica gel using Et2O yielded benzaldehyde (106mg, 99percent).

99 %Chromat.

Shin, Won Kyu; Kang, Daehoon; An, Duk Keun

Bulletin of the Korean Chemical Society, 2014 , vol. 35, # 7 p. 2169 - 2171 Title/Abstract Full Text View citing articles Show Details

With Na(1+)*C12H27AlNO5(1-) in tetrahydrofuran; toluene T=0 - 20°C; 0.5 h; Hide Experimental Procedure

Partial Reduction of Esters to Corresponding Aldehydes.

General procedure: The following experimental procedure for the partial reduction of ethyl benzoate to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07 mL, 0.5 mmol) and THF (5 mL). After cooling to 0 °C, cis-2,6dimethylmorpholine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at the room temperature. The reaction was stopped aqueous 1 N HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The ether layer was dried over anhydrous magnesium sulfate. GC analysis showed a 98percent yield of benzaldehyde. All products in Table 1 were confirmed through comparison with GC data of authentic sample.

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Chen, Ying-Zhe; Ni, Ching-Wen; Teng, Fu-Lin; Ding, Yi-Shun; Lee, Tunng-Hsien; Ho, Jinn-Hsuan

Tetrahedron, 2014 , vol. 70, # 9 p. 1748 - 1762 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: triphenylphosphine; 18-crown-6 ether; potassium carbonate / benzene; dichloromethane / 20 °C / |Reflux 2: potassium tert-butylate / tetrahydrofuran / 3 h / 40 °C / |Sealed tube; |Inert atmosphere; |Irradiation View Scheme

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A: 8% B: 12%

With potassium tert-butylate in tetrahydrofuran

T=40°C; 3 h; Sealed tubeInert atmosphereIrradiation;

Chen, Ying-Zhe; Ni, Ching-Wen; Teng, Fu-Lin; Ding, Yi-Shun; Lee, Tunng-Hsien; Ho, Jinn-Hsuan

Tetrahedron, 2014 , vol. 70, # 9 p. 1748 - 1762

Hide Experimental Procedure

Title/Abstract Full Text View citing articles Show Details

4.6.1 Photolysis of 1h in the presence of tBuOK/dried THF

A total of five identical samples were prepared, each of which contained 1h (20 mg), tBuOK (0.5 g), and dried THF (20 mL) in a quartz tube (1.5×20 cm). The tubes were sealed with septa and sonicated and shaken to suspend the undissolved particles. Then, the solution was bubbled with nitrogen gas for 20 min to remove dissolved oxygen. The sample was irradiated with 300 nm UV light at ambient temperature (approximately 40 °C) for 3 h. After irradiation, the five samples were combined, and 500 mL of water was added to the solution. The resulting solution was extracted with ethyl acetate several times, and the organic layers were combined and dried with anhydrous magnesium sulfate. The solvent was removed with a rotary evaporator, and the products were purified via chromatography using a mixed solution of ethyl acetate and hexane (1:10) for elution. Further purification was conducted via thin-layer-chromatography (TLC) to achieve an acceptable purity, 8.3 mg (8percent yield) of N3h and 10.8 mg (12percent yield) of 5h were obtained. 4.6.1.1 Naphthalen-2-yl-acetaldehyde N3h44 (0113) 1H NMR (500 MHz, CDCl3): δ 9.84 (t, J=2.4 Hz, 1H), 7.91–7.81 (m, 3H), 7.71 (s, 1H), 7.53–7.47 (m, 2H), 7.34 (dd, J=8.4, 1.8 Hz, 1H), 3.86 (d, J=2.4 Hz, 1H). 4.6.1.2 Naphthalene-2-carbaldehyde 5h45 (0114) 1H NMR (500 MHz, CDCl3): δ 10.18 (s, 1H), 8.02 (d, J=8.2 Hz, 1H), 7.97 (dd, J=8.6, 1.5 Hz, 1H), 7.95 (d, J=8.6 Hz, 2H), 7.92 (d, J=8.2 Hz, 1H), 7.66 (td, J=8.2, 1.3 Hz, 1H), 7.60 (td, J=8.2, 1.2 Hz, 1H).

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Rx-ID: 37949435 Find similar reactions

With nitric acid in water

Nemati, Firouzeh; Ghiyaei, Ali Ghorbani Gharjeh; Notash, Behrouz; Shayegan, Mojtaba Hajiloo; Amani, Vahid

Tetrahedron Letters, 2014 , vol. 55, # 25 p. 3572 - 3575 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 37949436 Find similar reactions

Nemati, Firouzeh; Ghiyaei, Ali Ghorbani Gharjeh; Notash, Behrouz; Shayegan, Mojtaba Hajiloo; Amani, Vahid

Tetrahedron Letters, 2014 , vol. 55, # 25 p. 3572 - 3575 Title/Abstract Full Text View citing articles Show Details

With nitric acid in water

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Rx-ID: 38112141 Find similar reactions

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81%

Stage #1: With triethylsilane; palladium diacetate; sodium carbonate; 2-dicyclohexylphosphino-1,1'-biphenyl in N,N-dimethyl-formamide

T=65°C; 8 h; Inert atmosphereSealed tubeGreen chemistry; Stage #2: With water

Green chemistry;

Jiang, Xiao; Wang, Jin-Mei; Zhang, Ying; Chen, Zhong; Zhu, Yong-Ming; Ji, Shun-Jun

Organic Letters, 2014 , vol. 16, # 13 p. 3492 - 3495 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39989068 Find similar reactions

70%

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With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane in N,N-dimethyl-formamide

T=20 - 100°C; P=15001.5 Torr; 20 h; Inert atmosphereAutoclave;

Natte, Kishore; Dumrath, Andreas; Neumann, Helfried; Beller, Matthias

Angewandte Chemie - International Edition, 2014 , vol. 53, # 38 p. 10090 - 10094 Angew. Chem., 2015 , vol. 126, # 38 p. 10254 - 10258,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 828372 Find similar reactions

84%

With triethylsilane; tris(2,4,6-trimethylphenyl)phosphine; bis(dibenzylideneacetone)-palladium(0) in toluene

T=40°C; 1.5 h; Schlenk techniqueInert atmosphere;

Fujihara, Tetsuaki; Cong, Cong; Iwai, Tomohiro; Terao, Jun; Tsuji, Yasushi

Synlett, 2012 , vol. 23, # 16 art. no. ST-2012-U0571-L, p. 2389 - 2392 Title/Abstract Full Text View citing articles Show Details

81%

With sodium tris(tert-butoxo)aluminium hydride in tetrahydrofuran; diethylene glycol dimethyl ether

T=-78°C; 3 h;

Cha, Jin Soon; Brown, Herbert C.

Journal of Organic Chemistry, 1993 , vol. 58, # 17 p. 4732 - 4734 Title/Abstract Full Text View citing articles Show Details

81%

With polymethylhydrosiloxane; trifuran-2-yl-phosphane; tetrabutyl ammonium fluoride; potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran; water

T=20°C; 1 h;

Lee, Kyoungsoo; Maleczka Jr., Robert E.

Organic Letters, 2006 , vol. 8, # 9 p. 1887 - 1888 Title/Abstract Full Text View citing articles Show Details

65%

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) in benzene

1 h; Ambient temperature;

Four, P.; Guibe, F.

Journal of Organic Chemistry, 1981 , vol. 46, # 22 p. 4439 - 4445 Title/Abstract Full Text View citing articles Show Details

65%

With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) in benzene

2 h; Ambient temperature;

Guibe, Francois; Four, Pierre; Riviere, Henriette

Journal of the Chemical Society, Chemical Communications, 1980 , # 10 p. 432 - 433 Title/Abstract Full Text View citing articles Show Details

With triethylsilane; triphenylphosphine; palladium diacetate in N,N-dimethyl-formamide

T=60°C; 12 h;

Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto

Synlett, 2006 , # 6 p. 869 - 872 Title/Abstract Full Text View citing articles Show Details

With Pd-BaSO4; sulfurated quinoline; xylene

T=140 - 150°C; Hydrogenation;

Hershberg; Cason

Organic Syntheses, 1941 , vol. 21, p. 84 Full Text View citing articles Show Details

With lithium tri-t-butoxyaluminum hydride

Brown; Rao

Journal of the American Chemical Society, 1958 , vol. 80, p. 5368,5377 Full Text View citing articles Show Details

98 % Chromat.

Stage #1: With aluminium hydride in tetrahydrofuran

T=20°C; Metallation; 1 h; Stage #2: With dipyridinium dichromate in tetrahydrofuran; dichloromethane

T=20°C; Oxidation; 3 h;

Cha, Jin Soon; Kim, Jong Mi; Chun, Joong Hyun; Kwon, Oh Oun; Kwon, Sang Yong; Han, Sung Wook

Organic Preparations and Procedures International, 1999 , vol. 31, # 2 p. 204 - 207 Title/Abstract Full Text View citing articles Show Details

92 %Chromat.

Stage #1: With morpholine; diisobutylaluminium hydride in tetrahydrofuran; hexane

T=0°C; 0.166667 h; Inert atmosphere; Stage #2: With LDBMA in tetrahydrofuran; hexane

T=0°C; 0.166667 h; Hide Experimental Procedure

Park, Jae Kyo; Shin, Won Kyu; An, Duk Keun

Tetrahedron Letters, 2013 , vol. 54, # 24 p. 3199 - 3203 Title/Abstract Full Text View citing articles Show Details

58%

Partial reduction of acid chlorides to corresponding aldehydes

General procedure: The following experimental procedure for the partial reduction of benzoyl chloride to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.11 mL, 1.25 mmol) and THF (10 mL). After cooling to 0 °C, DIBALH (1.2 mL, 1.0 M in hexane, 1.2 mmol) was added dropwise and the mixture was stirred for 3 h at the same temperature. Benzoyl chloride (0.116 mL, 1.0 mmol) was added slowly to the reaction mixture, which was stirred for 10 min. Then, LDBMA (3.3 mL, 0.46 M in hexane–THF, 1.5 mmol) was added and the mixture was stirred for 10 min again. The reaction was stopped by aqueous 1 N HCl (10 mL) and extracted with diethyl ether (2 × 10 mL). The combined organic layers were dried over MgSO4. GC analysis showed a 99percent yield of benzaldehyde. All products in Table 2 were confirmed through comparison with GC data of authentic sample.

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Rx-ID: 854704 Find similar reactions

74%

With methylphenylsilane; 2,2-dimethylpropanoic anhydride; Tri(p-tolyl)phosphine; bis(dibenzylideneacetone)-palladium(0) in toluene

T=60°C; 20 h; Schlenk techniqueInert atmosphere;

Fujihara, Tetsuaki; Cong, Cong; Terao, Jun; Tsuji, Yasushi

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 17 p. 3420 - 3424 Title/Abstract Full Text View citing articles Show Details

70%

With potassium phosphate; sodium hypophosphite; 2,2-dimethylpropanoic anhydride; palladium diacetate; PCy3 in tetrahydrofuran

T=60°C; 16 h;

Goossen, Lukas J; Ghosh, Keya

Chemical communications (Cambridge, England), 2002 , # 8 p. 836 - 837 Title/Abstract Full Text View citing articles Show Details

45%

With thexylbromoborane dimethyl sulfide complex in carbon disulfide; dichloromethane

T=-20 - 20°C; 1 h;

Cha, Jin Soon; Kim, Jin Euog; Oh, Se Yeon; Lee, Jae Cheol; Lee, Kwang Woo

Tetrahedron Letters, 1987 , vol. 28, # 21 p. 2389 - 2392 Title/Abstract Full Text View citing articles Show Details

With sodium amalgam; boric acid; sodium sulfite

Weil; Ostermeier

Chemische Berichte, 1921 , vol. 54, p. 3218 Full Text View citing articles Show Details

Weil

Chemische Berichte, 1911 , vol. 44, p. 3060

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Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 2 h / 20 °C 2.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.5 h / 0 - 20 °C 3.1: 1-(Trimethylsilyl)imidazole / toluene / 6 h / 55 °C / |Inert atmosphere 3.2: 1 h / 20 °C / |Inert atmosphere View Scheme

Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru

Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119 Title/Abstract Full Text View citing articles Show Details

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With dihydrogen peroxide; tantalum pentachloride; sodium iodide in water; ethyl acetate

T=20°C; 24 h; Hide Experimental Procedure

Rx-ID: 9334850 Find similar reactions

Kirihara, Masayuki; Noguchi, Takuya; Okajima, Nobuhiro; Naito, Sayuri; Ishizuka, Yuki; Harano, Aiko; Tsukiji, Hiroyuki; Takizawa, Ryu Tetrahedron, 2012 , vol. 68, # 5 p. 1515 - 1520 Title/Abstract Full Text View citing articles Show Details

6.2. General procedure for the deprotection of dithioacetals catalyzed by NaI-TaCl5

General procedure: A mixture of 1 (1.0 mmol), tantalum chloride (35.8 mg, 0.10 mmol), sodium iodide (15.0 mg, 0.10 mmol), and 30percent hydrogen peroxide (0.46 ml, 4.0 mmol) in ethyl acetate (6 ml) and water (6 ml) was stirred at room temperature. The reaction was monitored by thin layer chromatography (TLC). After 1 disappeared on TLC, saturated aqueous sodium thiosulfate (4 ml), and saturated aqueous sodium bicarbonate (4 ml) were added to the reaction mixture. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (25 ml.x.3). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, and evaporated. Chromatography on silica gel gave a pure product. 98%

With iron (III) acetylacetonate; dihydrogen peroxide; sodium iodide in water; ethyl acetate

T=20°C; 1.3 h; Hide Experimental Procedure

Kirihara, Masayuki; Suzuki, Satoshi; Ishizuka, Yuki; Yamazaki, Kento; Matsushima, Ryoji; Suzuki, Takaya; Iwai, Toshiaki

Tetrahedron Letters, 2013 , vol. 54, # 40 p. 5477 - 5480 Title/Abstract Full Text View citing articles Show Details

General procedure for the deprotection of dithioacetals with 30percent H2O2 (the slowaddition using a syringe pump) catalyzed by Fe(acac)3–NaI

General procedure: A mixture of adithioacetal (2.0 mmol), Fe(acac)3 (70.6 mg, 0.20 mmol) and sodium iodide(300 mg, 2.0 mmol) in ethyl acetate (6 ml) and water (6 ml) was stirred atroom temperature. To this mixture, 30percent H2O2 was added slowly using a syringepump (4 ml/30 min). The reaction was monitored by thin layerchromatography via TLC. After the dithioacetal disappeared from the TLC,saturated aqueous sodium thiosulfate (4 ml), was added to the reactionmixture. The organic layer was separated and the aqueous phase was extractedwith ethyl acetate (10 ml 3). The combined organic phase was washed withbrine, dried over anhydrous sodium sulfate, and evaporated. Chromatographyon silica gel gave a pure product. 96%

Stage #1: With acetyl chloride; sodium nitrite in dichloromethane

T=0 - 5°C; 0.25 h; Stage #2: With water in dichloromethane

T=0 - 20°C; 0.5 h;

Khan, Abu T.; Mondal, Ejabul; Sahu, Priti R.

Synlett, 2003 , # 3 p. 377 - 381 Title/Abstract Full Text View citing articles Show Details

94%

With 2,4,6-trichloro-1,3,5-triazine; dimethyl sulfoxide in dichloromethane

T=20°C; 1 h;

Karimi, Babak; Hazarkhani, Hassan

Synthesis, 2003 , # 16 p. 2547 - 2551 Title/Abstract Full Text View citing articles Show Details

96 %Spectr.

With p-benozquinone; sodium iodide in water; acetonitrile

T=100°C; 48 h; Hide Experimental Procedure

Inamoto, Kiyofumi; Yamada, Tetsuya; Kato, Sei-Ichi; Kikkawa, Shoko; Kondo, Yoshinori

Tetrahedron, 2013 , vol. 69, # 44 p. 9192 - 9199 Title/Abstract Full Text View citing articles Show Details

4.3.1 Representative procedure for deprotection of 1,3-dithianes (Table 2, entry 3)

General procedure: A mixture of 2-(2-methoxyphenyl)-1,3-dithiane (1c) (0.11 g, 0.50mmol), 1,4-benzoquinone (64.8 mg, 0.60 mmol), and NaI (0.70 mg, 0.005 mmol) in MeCN (2mL) and H2O (0.2mL) was stirred at 100°C for 24 h. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (eluent: hexane/AcOEt=15/1) to give 2-methoxybenzaldehyde (2c, 66.5mg, 98percent) as colorless oil.

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Rx-ID: 22070745 Find similar reactions

With copper(l) iodide; oxygen in dimethyl sulfoxide

T=120°C; 27 h; chemoselective reaction;

Zhang, Lin; Bi, Xihe; Guan, Xiaoxue; Li, Xingqi; Liu, Qun; Barry, Badru-Deen; Liao, Peiqiu

Angewandte Chemie - International Edition, 2013 , vol. 52, # 43 p. 11303 - 11307 Angew. Chem., 2013 , vol. 125, # 43 p. 11513 - 11517,5 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: pyridine; potassium permanganate; aqueous KOH-solution 2: N,N-dimethyl-p-toluidine View Scheme

Cymerman-Craig et al.

Australian Journal of Chemistry, 1956 , vol. 9, p. 222,226 Full Text Show Details

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Multi-step reaction with 3 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 2 h / 20 °C 2.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.5 h / 0 - 20 °C 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / 20 °C / |Inert atmosphere 3.2: 1 h / 20 °C / |Inert atmosphere View Scheme

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Rx-ID: 35357872 Find similar reactions

Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru

Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.5 h / 0 - 20 °C 2.1: N-(trimethylsilyl)-imidazole / toluene / 6 h / 55 °C / |Inert atmosphere 2.2: 1 h / 20 °C / |Inert atmosphere View Scheme

Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru

Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 0.5 h / 0 - 20 °C 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / 20 °C / |Inert atmosphere 2.2: 1 h / 20 °C / |Inert atmosphere View Scheme

Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru

Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 35357886 Find similar reactions

Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru

Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119 Title/Abstract Full Text View citing articles Show Details

Stage #1: With N-(trimethylsilyl)-imidazole in toluene

T=55°C; 6 h; Inert atmosphere; Stage #2: With citric acid in methanol; toluene

T=20°C; 1 h; Inert atmosphere; Reagent/catalystTemperature;

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Synthesize Find similar Rx-ID: 35357887

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A: 45% B: 46%

Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene in toluene

T=20°C; 6 h; Inert atmosphere; Stage #2: With citric acid in methanol; toluene

T=20°C; 1 h; Inert atmosphere; Reagent/catalystTemperature;

Iwai, Yuri; Ozaki, Takashi; Takita, Ryo; Uchiyama, Masanobu; Shimokawa, Jun; Fukuyama, Tohru

Chemical Science, 2013 , vol. 4, # 3 p. 1111 - 1119 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 35585999 Find similar reactions

79%

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Stage #1: N,N-dimethyl-1-(naphthalen-2-yl)methanamine With di-isopropyl azodicarboxylate

T=0 - 20°C; 1 h; Schlenk technique; Stage #2: 1-fluoro-1,1-bis(phenylsulfonyl)methane in N,N-dimethyl-formamide

T=60°C; 30 h; regioselective reaction;

Huang, Weizhou; Ni, Chuanfa; Zhao, Yanchuan; Hu, Jinbo

New Journal of Chemistry, 2013 , vol. 37, # 6 p. 1684 - 1687 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 36051540 Find similar reactions

77%

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With triethylsilane; palladium diacetate; sodium carbonate; 1,4-di(diphenylphosphino)-butane in N,N-dimethyl-formamide

T=85°C; Inert atmosphereSealed tube;

Ueda, Tsuyoshi; Konishi, Hideyuki; Manabe, Kei

Angewandte Chemie - International Edition, 2013 , vol. 52, # 33 p. 8611 - 8615 Angew. Chem., 2013 , vol. 125, # 33 p. 8773 - 8777,5 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 36088450 Find similar reactions

A: 86 %Spectr.

With pyridine-2-carboxylic acid; iron sulphate heptahydrate; dihydrogen peroxide

T=20 - 60°C; 12 h; Schlenk techniqueMolecular sieve;

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Ray, Ritwika; Chowdhury, Abhishek Dutta; Lahiri, Goutam Kumar

ChemCatChem, 2013 , vol. 5, # 8 p. 2158 - 2161 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10295056 Find similar reactions

92%

With TBCA in acetonitrile

T=20°C; 3.5 h;

Habibi, Davood; Zolfigol, Mohammad Ali; Faraji, Ali Reza; Rahmani, Payam

Monatshefte fur Chemie, 2012 , vol. 143, # 5 p. 809 - 814 Title/Abstract Full Text View citing articles Show Details

66%

With cetyltrimethylammonium bromate in 1,4-dioxane

5 h; Heating;

Baruah, Akashi; Nath, Utpal; Das, Satya Sandhya; Das, Pranab Jyoti

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006 , vol. 45, # 9 p. 2157 - 2160 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 11100433 Find similar reactions

A: 75% B: 9%

With tert-butyl 1-hydroxy-2-methyl-6-trifluoromethyl-1H-indole-3-carboxylate; oxygen; copper(l) chloride in N,N-dimethyl-formamide

T=50°C; P=760.051 Torr; 12 h; Hide Experimental Procedure

Shen, Shu-Su; Kartika, Vita; Tan, Ying Shan; Webster, Richard D.; Narasaka, Koichi

Tetrahedron Letters, 2012 , vol. 53, # 8 p. 986 - 990 Title/Abstract Full Text View citing articles Show Details

2.2 General procedure for aerobic oxidation of allylic and benzylic alcohols

General procedure: To a 10 mL Schlenk tube, NHI-1 (0.2 mmol, 63 mg) and CuCl (0.2 mmol, 19.6 mg) and DMF (2 mL) were added and stirred at 50 °C for about 30 min to form a dark red solution. Alcohol 11 (2 mmol) was added, the mixture was left to stir at 50 °C under an oxygen balloon (1 atm). The reaction progress was monitored by TLC or GC. After completion, the mixture was allowed to cool to room temperature, quenched with 1M HCl and diluted with H2O (50 mL), extracted with EtOAc (EA) (10 mL .x. 3), the combined organic layer was washed with brine and dried over MgSO4, the crude was purified by flash column chromatography (EtOAc : hexane = 1 : 10 to 1: 3) to afford ketone or aldehyde 12. A: 51% B: 41%

With 2,9-dimethyl-1,10-phenanthroline; oxygen; sodium hydrogencarbonate; gold(I) chloride in water

T=100°C; P=38002.6 Torr; 24 h;

Li, Huanrong; Guan, Bingtao; Wang, Wenjin; Xing, Dong; Fang, Zhao; Wan, Xiaobing; Yang, Liping; Shi, Zhangjie

Tetrahedron, 2007 , vol. 63, # 35 p. 8430 - 8434 Title/Abstract Full Text View citing articles Show Details

With oxygen; nitric acid in 1,4-dioxane; water

T=90°C; 5 h; chemoselective reaction;

Kuang, Yongbo; Islam, Nazrul M.; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki

Angewandte Chemie - International Edition, 2010 , vol. 49, # 2 p. 436 - 440 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29441785 Find similar reactions

93%

With oxygen; palladium diacetate; toluene-4-sulfonic acid in water

T=100°C; P=6080.41 Torr; 24 h;

Wang, Azhong; Jiang, Huanfeng

Journal of Organic Chemistry, 2010 , vol. 75, # 7 p. 2321 - 2326 Title/Abstract Full Text View citing articles Show Details

10%

With oxygen; copper diacetate; palladium dichloride in N,N-dimethyl acetamide

T=140°C; P=760.051 Torr; 48 h;

Liu, Yan-Yun; Song, Ren-Jie; Wu, Cui-Yan; Gong, Lu-Bin; Hu, Ming; Wang, Zhi-Qiang; Xie, Ye-Xiang; Li, Jin-Heng

Advanced Synthesis and Catalysis, 2012 , vol. 354, # 2-3 p. 347 - 353 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 33246080 Find similar reactions

A: 70% B: 4%

Zhang, Chun; Xu, Zejun; Shen, Tao; Wu, Guolin; Zhang, Liangren; Jiao, Ning

Organic Letters, 2012 , vol. 14, # 9 p. 2362 - 2365 Title/Abstract Full Text View citing articles Show Details

With oxygen; Mn(OAc)3•2H2O in toluene

T=90°C; P=760.051 Torr; 12 h;

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Synthesize Find similar Rx-ID: 33465232 Find similar reactions

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A: 45% B: 10% C: 15%

Stage #1: 2-bromo-naphthalene With n-butyllithium in tetrahydrofuran; hexane

T=-78°C; 0.5 h; Stage #2: formic acid ethyl ester in tetrahydrofuran; hexane

T=-78°C; 3 h; Stage #3: With ethanol; iodine; potassium carbonate in hexane

T=-78 - 20°C; 18 h; Hide Experimental Procedure

Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo

Tetrahedron, 2012 , vol. 68, # 24 p. 4701 - 4709 Title/Abstract Full Text View citing articles Show Details

4.2. Typical procedure for one-pot conversion of aromatic bromides into aromatic ethyl esters with ethyl formate

General procedure: n-BuLi (1.67 M solution in hexane, 1.32 mL, 2.2 mmol) was added dropwise into a solution of p-bromochlorobenzene (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, ethyl formate (1.6 mL, 20 mmol) was added to the mixture and the obtained mixture was stirred at -78 °C. After 3 h at the same temperature, I2 (1523 mg, 6 mmol), K2CO3 (1382 mg, 10 mmol) and EtOH (3 mL) were added at -78 °C and the mixture was stirred for 14 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide ethyl 4-chlorobenzoate in 77percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure ethyl 4-chloro-1-benzoate as a colorless oil.

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Rx-ID: 34265970 Find similar reactions

With tetrafluoroboric acid; iodosylbenzene in 1,4-dioxane; water

T=20°C; 144 h;

Havare, Nizam; Plattner, Dietmar A.

Organic Letters, 2012 , vol. 14, # 19 p. 5078 - 5081,4 Title/Abstract Full Text Show Details

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Rx-ID: 34265971 Find similar reactions

Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / |Inert atmosphere 2: iodosylbenzene; tetrafluoroboric acid / water; 1,4-dioxane / 144 h / 20 °C View Scheme

Havare, Nizam; Plattner, Dietmar A.

Organic Letters, 2012 , vol. 14, # 19 p. 5078 - 5081,4 Title/Abstract Full Text Show Details

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A: 22 %Chromat. B: 34 %Chromat. C: 10 %Chromat.

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With Fe(5,10,15-tris(2.6-dichlorophenyl)corrole(3-))Cl; dihydrogen peroxide; 1-n-butyl-3-methylimidazolium tetrafluoroborate in dichloromethane; water

T=20°C; 5 h; Hide Experimental Procedure

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Kumari, Pratibha; Nagpal, Ritika; Chauhan, Shive M.S.

Catalysis Communications, 2012 , vol. 29, p. 15 - 20 Title/Abstract Full Text View citing articles Show Details

2.2 Representative procedure for the oxidation of PAHs (1–4) with H2O2 catalyzed by iron (IV) corroles (17a–17e) in CH2Cl2/ IL (1:1,v/v)

General procedure: To the solution of PAHs (1–4) (4.0 mmole) and iron (IV) corrole (17a–17e) (0.04 mmole) in CH2Cl2: IL (1:1, v/v) (24 mL), H2O2 (30percent in water, 12.0 mmole) was added in small aliquots and the reaction mixture was stirred for 5 h at room temperature. The progress of the reaction was examined by the analysis of thin layer chromatography (TLC). The solvent was removed under reduced pressure and the reaction mixture was extracted with ethyl acetate. The catalyst (17a–17e) immobilized in IL layer was dried and reused for the oxidations of PAHs. The ethyl acetate layer was concentrated under reduced pressure and all the components were separated by preparative TLC. The yield of different oxidized products was analyzed by HPLC in methanol/ water (1:1, v/v) as solvent, by comparing the retention time with authentic samples. All the oxidized products were characterized by 1H NMR, IR and MS spectroscopic techniques which gave the satisfactory results with the reported data. A: 22 %Chromat. B: 34 %Chromat. C: 10 %Chromat.

With Fe(5,10,15-tris(2.6-dichlorophenyl)corrole(3-))Cl; dihydrogen peroxide; 1-n-butyl-3-methylimidazolium tetrafluoroborate in dichloromethane; water

T=20°C; 5 h; Hide Experimental Procedure

Kumari, Pratibha; Nagpal, Ritika; Chauhan, Shive M.S.

Catalysis Communications, 2012 , vol. 29, p. 15 - 20 Title/Abstract Full Text View citing articles Show Details

2.2 Representative procedure for the oxidation of PAHs (1–4) with H2O2 catalyzed by iron (IV) corroles (17a–17e) in CH2Cl2/ IL (1:1,v/v)

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A: 25 %Chromat. B: 5 %Chromat. C: 37 %Chromat. D: 12 %Chromat.

With (tpfc)FeCl; dihydrogen peroxide; 1-n-butyl-3-methylimidazolium tetrafluoroborate in dichloromethane; water

T=20°C; 5 h; SolventReagent/catalyst; Hide Experimental Procedure

Kumari, Pratibha; Nagpal, Ritika; Chauhan, Shive M.S.

Catalysis Communications, 2012 , vol. 29, p. 15 - 20 Title/Abstract Full Text View citing articles Show Details

2.2 Representative procedure for the oxidation of PAHs (1–4) with H2O2 catalyzed by iron (IV) corroles (17a–17e) in CH2Cl2/ IL (1:1,v/v)

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Rx-ID: 2158101 Find similar reactions

With water in acetonitrile

0.333333 h; UV-irradiation;

Thevenet, Damien; Neier, Reinhard

Helvetica Chimica Acta, 2011 , vol. 94, # 2 p. 331 - 346 Title/Abstract Full Text View citing articles Show Details

With dimethylboron bromide; sodium hydrogencarbonate

1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;

Guindon, Yvan; Yoakim, Christiane; Morton, Howard E.

Journal of Organic Chemistry, 1984 , vol. 49, # 21 p. 3912 - 3920 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 26050638 Find similar reactions

92%

With MoO2(S2CNEt2)2; oxygen in water

15 h; Heating;

Maddani, Mahagundappa; Prabhu, Kandikere Ramaiah

Tetrahedron Letters, 2008 , vol. 49, # 29-30 p. 4526 - 4530 Title/Abstract Full Text View citing articles Show Details

74 %Chromat.

With di[(2,4-bis-tert-butyl-1-methoxy-3-neopentylcyclopentadienyl)dichlororuthenium(III)]; water in acetonitrile

T=75°C; 7 h; Inert atmosphere;

Risse, Julie; Scopelliti, Rosario; Severin, Kay

Organometallics, 2011 , vol. 30, # 12 p. 3412 - 3418 Title/Abstract Full Text View citing articles Show Details

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A: 10 %Spectr. B: 65 %Spectr.

Thevenet, Damien; Neier, Reinhard

Helvetica Chimica Acta, 2011 , vol. 94, # 2 p. 331 - 346 Title/Abstract Full Text View citing articles Show Details

in chloroform-d1

T=26°C; 1 h; UV-irradiation;

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Rx-ID: 30756453 Find similar reactions

Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: acetic acid / 2 h / 80 °C / Inert atmosphere View Scheme

Safa, Kazem D.; Behmagham, Farnaz; Ghorbanpour, Khatereh

Journal of Organometallic Chemistry, 2011 , vol. 696, # 9 p. 1840 - 1844 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 62 %Chromat.

Synthesize Find similar

Rx-ID: 30756458 Find similar reactions

Safa, Kazem D.; Behmagham, Farnaz; Ghorbanpour, Khatereh

Journal of Organometallic Chemistry, 2011 , vol. 696, # 9 p. 1840 - 1844 Title/Abstract Full Text View citing articles Show Details

With acetic acid

T=80°C; 2 h; Inert atmosphere;

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Synthesize Find similar Rx-ID: 28828087 Find similar reactions

A: 66% B: 9%

With ammonium hydrogen carbonate in 1,3,5-trimethyl-benzene

T=140°C; P=4560.31 Torr; 3 h;

Yamaguchi, Kazuya; He, Jinling; Oishi, Takamichi; Mizuno, Noritaka

Chemistry - A European Journal, 2010 , vol. 16, # 24 p. 7199 - 7207

Title/Abstract Full Text View citing articles Show Details

A: 29% B: 38%

With ammonium acetate in 1,3,5-trimethyl-benzene

T=140°C; P=4560.31 Torr; 3 h;

Yamaguchi, Kazuya; He, Jinling; Oishi, Takamichi; Mizuno, Noritaka

Chemistry - A European Journal, 2010 , vol. 16, # 24 p. 7199 - 7207 Title/Abstract Full Text View citing articles Show Details

With ammonia; oxygen in tetrahydrofuran

T=120°C; P=4560.31 Torr; 1 h;

Oishi, Takamichi; Yamaguchi, Kazuya; Mizuno, Noritaka

Angewandte Chemie, International Edition, 2009 , vol. 48, # 34 p. 6286 - 6288 Angewandte Chemie, 2009 , vol. 121, # 34 p. 6404 - 6406 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 29150610 Find similar reactions

B: 75%

With oxygen; palladium dichloride in N,N-dimethyl acetamide; water

T=80°C; P=7600.51 Torr; 1 h; chemoselective reaction;

Bueno, Aline C.; De Souza, Agatha O.; Gusevskaya, Elena V.

Advanced Synthesis and Catalysis, 2009 , vol. 351, # 14-15 p. 2491 - 2495 Title/Abstract Full Text View citing articles Show Details

With [PdCl2(tBu-BINC)]; oxygen in N,N-dimethyl acetamide; water

T=70°C; Wacker oxidation; P=760.051 Torr; 70 h;

Naik, Anu; Meina, Liu; Zabel, Manfred; Reiser, Oliver

Chemistry - A European Journal, 2010 , vol. 16, # 5 p. 1624 - 1628 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 31425706 Find similar reactions

Stage #1: With N-bromosuccinmide in tetrahydrofuran; water

T=0°C; 0.333333 h; Stage #2: With silver nitrate in tetrahydrofuran; water

T=20°C; 4 h; optical yield given as percent dediastereoselective reaction;

Yin, Biaolin; Lai, Jinqiang; Zhang, Zeren; Wu, Yulin

Chinese Journal of Chemistry, 2010 , vol. 28, # 12 p. 2335 - 2338 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 31425707 Find similar reactions

Stage #1: With 3-chloro-benzenecarboperoxoic acid in tetrahydrofuran; water

Yin, Biaolin; Lai, Jinqiang; Zhang, Zeren; Wu, Yulin

Chinese Journal of Chemistry, 2010 , vol. 28, # 12 p. 2335 - 2338 Title/Abstract Full Text View citing articles Show Details

Stage #2: in dichloromethane

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Synthesize Find similar Rx-ID: 28480921 Find similar reactions

Mundal, Devon A.; Lutz, Kelly E.; Thomson, Regan J.

Organic Letters, 2009 , vol. 11, # 2 p. 465 - 468 Title/Abstract Full Text View citing articles Show Details

With copper(ll) bromide in acetonitrile

T=0°C; Inert atmosphere;

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Rx-ID: 29110218 Find similar reactions

With water; oxoammonium salt in acetonitrile

T=20°C; 8 h;

Pradhan, Priya P.; Bobbitt, James M.; Bailey, William F.

Journal of Organic Chemistry, 2009 , vol. 74, # 24 p. 9524 - 9527 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Rx-ID: 29222502 Find similar reactions

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With benzophenone in acetonitrile

T=20°C; Inert atmosphereUV-irradiationPhotolysis; Quantum yield; Reagent/catalystConcentration;

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Watanabe, Asako; Matsushita, Maya; Masuda, Aya; Igarashi, Tetsutaro; Sakurai, Tadamitsu

Heterocycles, 2009 , vol. 78, # 10 p. 2431 - 2437 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 29222505 Find similar reactions

With benzophenone in acetonitrile

T=20°C; Inert atmosphereUV-irradiationPhotolysis; Quantum yield;

Watanabe, Asako; Matsushita, Maya; Masuda, Aya; Igarashi, Tetsutaro; Sakurai, Tadamitsu

Heterocycles, 2009 , vol. 78, # 10 p. 2431 - 2437 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 93%

Synthesize Find similar

Rx-ID: 26010444 Find similar reactions

With tetrabutyl ammonium fluoride in tetrahydrofuran; N,N-dimethyl-formamide

T=50°C;

Cafiero, Lauren R.; Snowden, Timothy S.

Tetrahedron Letters, 2008 , vol. 49, # 17 p. 2844 - 2847 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27951231 Find similar reactions

B: 88%

With oxygen in toluene

20 h; Heating;

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Bishara, Ashgan; Rudi, Amira; Aknin, Maurice; Neumann, Drorit; Ben-Califa, Nathalie; Kashman, Yoel

Tetrahedron Letters, 2008 , vol. 49, # 37 p. 5437 - 5437 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 95%

Synthesize Find similar

Rx-ID: 28194803 Find similar reactions

Krohn, Karsten; Cludius-Brandt, Stephan

Synthesis, 2008 , # 15 art. no. T01408SS, p. 2369 - 2372 Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride in water; acetonitrile

T=20°C; 12 h;

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Rx-ID: 4469100 Find similar reactions

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94%

With palladium diacetate; (C8H17)3SiH; 1,3-bis-(diphenylphosphino)propane; triethylamine in N,N-dimethyl-formamide

T=70°C; 3.5 h;

Kotsuki, Hiyoshizo; Datta, Probal Kanti; Suenaga, Hitoshi

Synthesis, 1996 , # 4 p. 470 - 472 Title/Abstract Full Text View citing articles Show Details

69%

With pyridine; hydrogen; palladium diacetate; 1,3-bis-(diphenylphosphino)propane in N,N-dimethyl-formamide

T=80°C; P=15001.5 Torr; 24 h;

Brennfuhrer, Anne; Neumann, Helfried; Beller, Matthias

Synlett, 2007 , # 16 p. 2537 - 2540 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 10550571 Find similar reactions

With oxygen; [Acr+-Mes]ClO4- in dichloromethane

Irradiation; Title compound not separated from byproducts;

Griesbeck, Axel G.; Miyeon, Cho

Organic Letters, 2007 , vol. 9, # 4 p. 611 - 613 Title/Abstract Full Text View citing articles Show Details

With oxygen; 9,10-anthracenedicarbonitrile in acetonitrile

Irradiation; Title compound not separated from byproducts;

Griesbeck, Axel G.; Miyeon, Cho

Organic Letters, 2007 , vol. 9, # 4 p. 611 - 613 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 94 % Chromat.

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Rx-ID: 11172801 Find similar reactions

With naphthalene in tetrahydrofuran; hexane

T=0°C; 3 h;

Kim, Min Sung; Choi, Young Mi; An, Duk Keun

Tetrahedron Letters, 2007 , vol. 48, # 29 p. 5061 - 5064 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 10076537 Find similar reactions

B: 87%

With trichloroacetic acid in dichloromethane

T=28°C; 1.5 h;

Uemura, Minoru; Yagi, Kazunari; Iwasaki, Masayuki; Nomura, Kenichi; Yorimitsu, Hideki; Oshima, Koichiro

Tetrahedron, 2006 , vol. 62, # 15 p. 3523 - 3535 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 10076538 Find similar reactions

With trichloroacetic acid in dichloromethane

T=25 - 30°C; 12 h;

Uemura, Minoru; Yagi, Kazunari; Iwasaki, Masayuki; Nomura, Kenichi; Yorimitsu, Hideki; Oshima, Koichiro

Tetrahedron, 2006 , vol. 62, # 15 p. 3523 - 3535 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 25%

Synthesize Find similar

Rx-ID: 10162801 Find similar reactions

With triethylsilane; triphenylphosphine; palladium diacetate in N,N-dimethyl-formamide

T=60°C; 12 h;

Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto

Synlett, 2006 , # 6 p. 869 - 872 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 62%

Synthesize Find similar

With triethylsilane; triphenylphosphine; palladium diacetate in N,N-dimethyl-formamide

T=60°C; 12 h;

Rx-ID: 10164330 Find similar reactions

Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto

Synlett, 2006 , # 6 p. 869 - 872 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 91%

Synthesize Find similar

Rx-ID: 10199948 Find similar reactions

With triethylsilane; triphenylphosphine; palladium diacetate in N,N-dimethyl-formamide

T=60°C; 12 h;

Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto

Synlett, 2006 , # 6 p. 869 - 872 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 81%

Synthesize Find similar

Rx-ID: 10239470 Find similar reactions

With triethylsilane; triphenylphosphine; palladium diacetate in N,N-dimethyl-formamide

T=60°C; 12 h;

Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto

Synlett, 2006 , # 6 p. 869 - 872 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar 63%

Synthesize Find similar

Rx-ID: 10248099 Find similar reactions

With silver hexafluoroantimonate; magnesium oxide; triphenylphosphine in dichloromethane

T=20°C; Myers-Saito reaction; 11 h;

Zhao, Jing; Hughes, Colin O.; Toste, F. Dean

Journal of the American Chemical Society, 2006 , vol. 128, # 23 p. 7436 - 7437 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10545078 Find similar reactions

B: 46%

With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium in toluene

T=150°C; 72 h; Further byproducts given;

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Black, Phillip J.; Edwards, Michael G.; Williams, Jonathan M. J.

European Journal of Organic Chemistry, 2006 , # 19 p. 4367 - 4378 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12470942 Find similar reactions

Multi-step reaction with 2 steps 1: K2CO3 / CH2Cl2 / 20 °C 2: 91 percent / triethylsilane; PPh3 / Pd(OAc)2 / dimethylformamide / 12 h / 60 °C View Scheme

Nakanishi, Jun; Tatamidani, Hiroto; Fukumoto, Yoshiya; Chatani, Naoto

Synlett, 2006 , # 6 p. 869 - 872 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 781250 Find similar reactions

98%

With dipotassium hydrogenphosphate; Potassium benzeneselenite; dibenzo-18-crown-6 in acetonitrile

5 h; Heating;

Syper; Mlochowski

Synthesis, 1984 , vol. NO. 9, p. 747 - 752 Title/Abstract Full Text View citing articles Show Details

90%

With Bi(NO3)3; tetrabutyl ammonium fluoride

T=100°C; 3.5 h;

Khodaei, Mohammad Mehdi; Khosropour, Ahmad Reza; Jowkar, Mahbubeh

Synthesis, 2005 , # 8 art. no. Z21704SS, p. 1301 - 1304 Title/Abstract Full Text View citing articles Show Details

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With ethanol; 1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane

Dahn; Zoller

Helvetica Chimica Acta, 1952 , vol. 35, p. 1348,1351 Full Text View citing articles Show Details

With sodium hydrogen telluride; oxygen

1) DMF, 70 deg C, 2) room temperature; Yield given. Multistep reaction;

Bausch; Li

Synthetic Communications, 1996 , vol. 26, # 7 p. 1401 - 1404 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 8814638 Find similar reactions

A: 39.6 % Spectr. B: 9.2 % Spectr.

With titanocene difluoride; methylphenylsilane in toluene

T=20°C; Title compound not separated from byproducts;

Selvakumar, Kumaravel; Harrod, John F.

Angewandte Chemie - International Edition, 2001 , vol. 40, # 11 p. 2129 - 2131 Title/Abstract Full Text View citing articles Show Details

With titanocene difluoride; methylphenylsilane in toluene

T=25°C;

Rangareddy, Kesamreddy; Selvakumar, Kumaravel; Harrod, John F.

Journal of Organic Chemistry, 2004 , vol. 69, # 20 p. 6843 - 6850 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 8778508 Find similar reactions

95%

With cetyltrimethylammonium tribromide in dichloromethane

T=0 - 5°C; 0.0833333 h;

Mondal; Bose; Khan

Synlett, 2001 , # 6 p. 785 - 786 Title/Abstract Full Text View citing articles Show Details

95%

With dihydrogen peroxide; vanadium pentoxide; NH4Br in dichloromethane; water

T=0 - 5°C; 1.75 h;

Mondal, Ejabul; Bose, Gopal; Sahu, Priti Rani; Khan, Abu T.

Chemistry Letters, 2001 , # 11 p. 1158 - 1159 Title/Abstract Full Text View citing articles Show Details

95%

Stage #1: With acetyl chloride; sodium nitrite in dichloromethane

T=0 - 5°C; 0.25 h; Stage #2: With water in dichloromethane

Khan, Abu T.; Mondal, Ejabul; Sahu, Priti R.

Synlett, 2003 , # 3 p. 377 - 381 Title/Abstract Full Text View citing articles Show Details

T=0 - 20°C; 0.75 h;

84%

With ammonium heptamolybdate; dihydrogen peroxide; NH4Br; perchloric acid in dichloromethane; water

T=0 - 5°C; 0.5 h;

Khan; Boruwa; Mondal; Bose

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001 , vol. 40, # 11 p. 1039 - 1042 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 9031914 Find similar reactions

91%

With perchloric acid; dihydrogen peroxide; NH4Br; molibdic acid in dichloromethane

T=0 - 5°C; 4 h;

Mondal, Ejabul; Sahu, Priti Rani; Khan, Abu T.

Synlett, 2002 , # 3 p. 463 - 467 Title/Abstract Full Text View citing articles Show Details

90%

With tetrabutylammonium fluoride; dihydrogen peroxide; vanadium pentoxide in dichloromethane

T=0 - 5°C; 0.75 h;

Mondal, Ejabul; Sahu, Priti Rani; Bose, Gopal; Khan, Abu T.

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 8 p. 1026 - 1028 Title/Abstract Full Text View citing articles Show Details

84%

Stage #1: With acetyl chloride; sodium nitrite in dichloromethane

T=0 - 5°C; 0.25 h; Stage #2: With water in dichloromethane

T=0 - 20°C; 0.166667 h;

Khan, Abu T.; Mondal, Ejabul; Sahu, Priti R.

Synlett, 2003 , # 3 p. 377 - 381 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9338253 Find similar reactions

A: 39% B: 55%

Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.

Organic and Biomolecular Chemistry, 2003 , vol. 1, # 10 p. 1737 - 1740 Title/Abstract Full Text View citing articles Show Details

With N,N,N',N',N'',N''-hexamethylphosphoric triamide; iron(II) oxalate dihydrate

T=155 - 160°C; 0.583333 h; Product distribution; Further Variations:time;

Synthesize Find similar Rx-ID: 9340862 Find similar reactions

A: 19% B: 66%

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With N,N,N',N',N'',N''-hexamethylphosphoric triamide; iron(II) oxalate dihydrate

T=155 - 160°C; 1.33333 h;

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Khurana, Jitender M.; Chauhan, Sushma; Maikap, Golak C.

Organic and Biomolecular Chemistry, 2003 , vol. 1, # 10 p. 1737 - 1740 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9417568 Find similar reactions

A: 20% B: 60%

Ibrahim, Yehia A.; Al-Awadi, Nouria A.; Kual, Kamini

Tetrahedron, 2003 , vol. 59, # 29 p. 5425 - 5430 Title/Abstract Full Text View citing articles Show Details

T=700°C; P=0.02 Torr;

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Synthesize Find similar Rx-ID: 9598439 Find similar reactions

A: 30% B: 9% C: 24% D: 23%

T=750°C; P=1 Torr; Further byproducts given;

Olteanu, Emilia; Draghici, Constantin; Ciuculescu, Diana; Banciu, Mircea D.

Revue Roumaine de Chimie, 2003 , vol. 48, # 10 p. 829 - 833 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 2116347 Find similar reactions

90%

With zinc dichromate(VI) in dichloromethane

3 h; Ambient temperature;

Firouzabadi, H.; Sardarian, A. R.; Moosavipour, H.; Afshari, G. M.

Synthesis, 1986 , # 4 p. 285 - 288 Title/Abstract Full Text Show Details

87%

With zinc dinitrate; silica gel

deoxymation; 0.0666667 h; Irradiation;

Tamami; Kiasat

Synthetic Communications, 2000 , vol. 30, # 22 p. 4129 - 4135 Title/Abstract Full Text View citing articles Show Details

81%

With benzeneseleninic anhydride in tetrahydrofuran

T=40 - 50°C; 0.333333 h;

Barton, Derek H. R.; Lester, David J.; Ley, Steven V.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1212 - 1217 Title/Abstract Full Text View citing articles Show Details

81%

With iron(III) chloride in benzene

Heating;

Hangarge; Mane; Chavan; Shingare

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002 , vol. 41, # 6 p. 1302 - 1304 Title/Abstract Full Text View citing articles Show Details

56%

With Zn(BiO3)2 in toluene

1 h; Heating;

Firouzabadi; Mohammadpoor-Baltork

Synthetic Communications, 1994 , vol. 24, # 4 p. 489 - 494 Title/Abstract Full Text View citing articles Show Details

18%

With barium ferrate(VI) in benzene

1 h; Heating;

Firouzabadi, Habib; Mohajer, Daryoush; Entezari-Moghadam, Mohsen

Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 2185 - 2190 Title/Abstract Full Text Show Details

18%

With barium ferrate(VI) in benzene

1 h; Heating; Product distribution;

Firouzabadi, Habib; Mohajer, Daryoush; Entezari-Moghadam, Mohsen

Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 2185 - 2190 Title/Abstract Full Text Show Details

Synthesize Find similar 89%

Synthesize Find similar

With Amberlyst A-26 (OH-); dihydrogen peroxide in 1,4-dioxane

T=20°C; 10 h;

Rx-ID: 9131950 Find similar reactions

Lakouraj, Moslem M.; Movassagh, Barahman; Bahrami, Kyumars

Monatshefte fur Chemie, 2002 , vol. 133, # 9 p. 1193 - 1196

Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9134466 Find similar reactions

A: 8%

With phosphate buffer; Rhodococcus rhodochrous IFO 15564 in ethanol; water

T=30°C; pH=6.0; 18 h;

Kimura, Mayumi; Kuboki, Atsuhito; Sugai, Takeshi

Tetrahedron Asymmetry, 2002 , vol. 13, # 10 p. 1059 - 1068 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9157769 Find similar reactions

A: 45%

Kimura, Mayumi; Kuboki, Atsuhito; Sugai, Takeshi

Tetrahedron Asymmetry, 2002 , vol. 13, # 10 p. 1059 - 1068 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide; phosphate buffer; immobilized Burkholderia cepacia lipase in decane; water

T=30°C; pH=7.0; 38 h;

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Synthesize Find similar Rx-ID: 9157771 Find similar reactions

B: 35%

With nitrosylsulfuric acid in N,N-dimethyl-formamide

Kimura, Mayumi; Kuboki, Atsuhito; Sugai, Takeshi

T=20°C; 24 h; Title compound not separated from byproducts;

Tetrahedron Asymmetry, 2002 , vol. 13, # 10 p. 1059 - 1068 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9158139 Find similar reactions

A: 6%

With nitrosylsulfuric acid in N,N-dimethyl-formamide

T=0°C; 0.5 h; Title compound not separated from byproducts;

Kimura, Mayumi; Kuboki, Atsuhito; Sugai, Takeshi

Tetrahedron Asymmetry, 2002 , vol. 13, # 10 p. 1059 - 1068 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9158694 Find similar reactions

B: 4.6%

With nitrosyl sulfuric acid in N,N-dimethyl-formamide

T=20°C; 20 h; Title compound not separated from byproducts;

Kimura, Mayumi; Kuboki, Atsuhito; Sugai, Takeshi

Tetrahedron Asymmetry, 2002 , vol. 13, # 10 p. 1059 - 1068 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9210438 Find similar reactions

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A: 46% B: 16% C: 2%

With di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; 1,3-bis-(diphenylphosphino)propane; caesium carbonate in toluene

T=150°C; indirect Wittig reaction; 72 h;

Edwards, Michael G.; Williams, Jonathan M.J.

Angewandte Chemie - International Edition, 2002 , vol. 41, # 24 p. 4740 - 4743 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 9309625 Find similar reactions

A: 24%

With tetrabutylammomium bromide; palladium dichloride

T=120°C; 48 h;

Ganchegui, Benjamin; Bouquillon, Sandrine; Henin, Francoise; Muzart, Jacques

Tetrahedron Letters, 2002 , vol. 43, # 37 p. 6641 - 6644 Title/Abstract Full Text View citing articles Show Details