[DB] 1-(1-'[H,C]'-1-nitroprop-1-en-2-yl)-2,3,4,5,6-penta'GH'benzene by Asch

Query Query

Results

Date

140 reactions in Reaxys

2018-08-17 22h:31m:36s (UTC)

GH GH

NO 2

1. Query

L GH

[H,C]

Search as: Product, As drawn, Ignore stereo, No salts, No mixtures, No isotopes, No charges, No radicals, No additional rings ))

1/58

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N O

Rx-ID: 1119036 View in Reaxys 1/140 Yield

Conditions & References With sodium acetate Vasil'eva,O.S. et al.; Zhurnal Organicheskoi Khimii; vol. 14; nb. 7; (1978); p. 1420 - 1422,1326 - 1327 View in Reaxys in chloroform, triethylamine, Time= 3h, T= 20 °C Hall, Melanie; Stueckler, Clemens; Ehammer, Heidemarie; Pointner, Eva; Oberdorfer, Gustav; Gruber, Karl; Hauer, Bernard; Stuermer, Rainer; Kroutil, Wolfgang; Macheroux, Peter; Faber, Kurt; Advanced Synthesis and Catalysis; vol. 350; nb. 3; (2008); p. 411 - 418 View in Reaxys

788 mg

With triethylamine in chloroform, Time= 3h, T= 20 °C Durchschein, Katharina; Ferreira-Da Silva, Bianca; Wallner, Silvia; MacHeroux, Peter; Kroutil, Wolfgang; Glueck, Silvia Maria; Faber, Kurt; Green Chemistry; vol. 12; nb. 4; (2010); p. 616 - 619 View in Reaxys

788 mg

With triethylamine in chloroform, Time= 3h, T= 20 °C Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys O

N O

O N

Rx-ID: 2151208 View in Reaxys 2/140 Yield

Conditions & References With triethylamine in chloroform, Time= 3h, Ambient temperature, Yield given. Yields of byproduct given Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys

O N

O O

Rx-ID: 4531221 View in Reaxys 3/140 Yield 20 %

Conditions & References With N,N-diethylethylenediamine in benzene, Time= 24h, Heating Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288 View in Reaxys

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O O

N O

N O O O

N O

Rx-ID: 4935766 View in Reaxys 4/140 Yield

Conditions & References With 2,6-dimethylpyridine in chloroform-d1, Time= 3h, T= 22 °C Berg, Ulf; Butts, Craig P.; Eberson, Lennart; Hartshorn, Michael P.; Persson, Ola; Acta Chemica Scandinavica; vol. 52; nb. 6; (1998); p. 761 - 769 View in Reaxys O N O

Rx-ID: 7584101 View in Reaxys 5/140 Yield

Conditions & References α-Methylstyrol, NO, CCl4 (RT, Sonnenlicht) Tuaillon; Perrot; Helvetica Chimica Acta; vol. 61; (1978); p. 558,563 View in Reaxys 2-Phenyl-1-nitro-2-propylacetat, 1. NEt3, 2. HCl Bordwell et al.; Journal of Organic Chemistry; vol. 43; (1978); p. 3107,3108 View in Reaxys 1-Brom-2-phenyl-propen-(1), AgNO3 (Einschlussrohr, 130grad) Kaufman; Miller; Journal of Organic Chemistry; vol. 34; (1969); p. 1495 View in Reaxys (yield)75percent Kaufman; Miller; Journal of Organic Chemistry; vol. 34; (1969); p. 1495 View in Reaxys

N O

Rx-ID: 7584102 View in Reaxys 6/140 Yield

Conditions & References trans-Isomeren, Belichtung Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323 View in Reaxys

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O N O

Rx-ID: 7584103 View in Reaxys 7/140 Yield

Conditions & References Sousa et al.; Journal of Organic Chemistry; vol. 34; (1969); p. 3320,3323 View in Reaxys Miller et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2112,2118 View in Reaxys O

Rx-ID: 8574374 View in Reaxys 8/140 Yield 83 %

Conditions & References With sulfated zirconia, Time= 0.0333333h, microwave irradiation Bandgar; Kasture; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 40; nb. 12; (2001); p. 1239 - 1241 View in Reaxys

70 %

With potassium hydroxide, Agar-agar aqua gel in ethanol, acetonitrile, Time= 2h, T= 25 °C , Henry condensation Bandgar; Uppalla; Synthetic Communications; vol. 30; nb. 12; (2000); p. 2071 - 2075 View in Reaxys

O N O

Rx-ID: 8606278 View in Reaxys 9/140 Yield 84 %

Conditions & References With silver(I) nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in 1,2-dichloro-ethane, Time= 12h, T= 70 °C , Molecular sieve, stereoselective reaction Maity, Soham; Manna, Srimanta; Rana, Sujoy; Naveen, Togati; Mallick, Arijit; Maiti, Debabrata; Journal of the American Chemical Society; vol. 135; nb. 9; (2013); p. 3355 - 3358 View in Reaxys

62 %

General procedure for the synthesis of compounds 2 and 4 General procedure: To a 25 mL sealed tube were added alkenes 1 or 3 (0.5mmol) with NaNO2 (1.5 equiv.), K2S2O8 (2.0 equiv.), TEMPO (1.2 equiv.) and ClCH2CH2Cl (2 mL). The reaction mixture was stirred at 100 oC for 24 h. After the reaction was finished, the reaction was cooled to room temperature. Dichloromethane (2 mL) and water (5 mL) were added. The organic layer was separated, and the aqueous phase was extracted with dichloromethane (5 mL × 3). The combined organic layers were dried with anhydrous Na2SO4, filtered. After evaporating the solvent in vacuum, the residue was purified by column chromatography eluting with PE/EtOAc to obtain the pure nitroalkenes 2 or 4. With 2,2,6,6-tetramethyl-piperidine-N-oxyl, dipotassium peroxodisulfate, sodium nitrite in 1,2-dichloro-ethane, Time= 24h, T= 100 °C , Sealed tube, stereoselective reaction Zhao, An; Jiang, Qing; Jia, Jing; Xu, Bin; Liu, Yufeng; Zhang, Mingzhong; Liu, Qiang; Luo, Weiping; Guo, Cancheng; Tetrahedron Letters; vol. 57; nb. 1; (2016); p. 80 - 84 View in Reaxys

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With tetrafluoroboric acid, iodine, copper(II) oxide, sodium nitrite in acetonitrile, Time= 7h, T= 20 °C , Nitration Campos, Pedro J.; Garcia, Barbara; Rodriguez, Miguel A.; Tetrahedron Letters; vol. 41; nb. 6; (2000); p. 979 - 982 View in Reaxys With nitrosyl hydride in 1,2-dichloro-ethane, Time= 3h, T= 20 °C , p= 1500.15Torr , Inert atmosphere, Autoclave, optical yield given as percent de, regioselective reaction Jovel, Irina; Prateeptongkum, Saisuree; Jackstell, Ralf; Vogl, Nadine; Weckbecker, Christoph; Beller, Matthias; Advanced Synthesis and Catalysis; vol. 350; nb. 16; (2008); p. 2493 - 2497 View in Reaxys O

O N

O N O

Rx-ID: 9422854 View in Reaxys 10/140 Yield

Conditions & References

93 %

With 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, Time= 4h, Heating Jang, Yeong-Jiunn; Lin, Wen-Wei; Shih, Yuh-Kuo; Liu, Ju-Tsung; Hwang, Ming-Hsing; Yao, Ching-Fa; Tetrahedron; vol. 59; nb. 27; (2003); p. 4979 - 4992 View in Reaxys O

N O

Rx-ID: 9878760 View in Reaxys 11/140 Yield

Conditions & References With sodium hydroxide in chloroform, Time= 24h, T= 22 °C Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585 View in Reaxys With triethylamine in chloroform, T= 20 °C Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977 View in Reaxys With triethylamine in chloroform, Time= 3h, T= 20 °C Hall, Melanie; Stueckler, Clemens; Kroutil, Wolfgang; Macheroux, Peter; Faber, Kurt; Angewandte Chemie - International Edition; vol. 46; nb. 21; (2007); p. 3934 - 3937 View in Reaxys With sodium hydroxide in water, Time= 24h, T= 22 °C Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys With triethylamine in chloroform, Time= 3h, T= 20 °C

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Hall, Melanie; Stueckler, Clemens; Hauer, Bernhard; Stuermer, Rainer; Friedrich, Thomas; Breuer, Michael; Kroutil, Wolfgang; Faber, Kurt; European Journal of Organic Chemistry; nb. 9; (2008); p. 1511 - 1516 View in Reaxys With sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys O N

Rx-ID: 11067960 View in Reaxys 12/140 Yield 56 %

Conditions & References With strontium nitrate, nitric acid, Time= 1.5h, T= 20 °C , nitro Hunsdiecker reaction Ramgopal; Ramesh; Chakradhar; Reddy, N. Maasi; Rajanna; Tetrahedron Letters; vol. 48; nb. 23; (2007); p. 4043 - 4045 View in Reaxys O N

O N

Rx-ID: 11163845 View in Reaxys 13/140 Yield

Rx-ID: 11435259 View in Reaxys 14/140 Yield 65 %

Conditions & References [(E)-2-Nitrovinyl]benzene (2a); Typical Procedure General procedure: A mixture of styrene (0.104 g, 1.0 mmol), Claycop [0.605 g, 1.5 mmol containing 1.5 equiv Cu(NO3)2], TEMPO (0.0156 g, 20 molpercent), and 1,4-dioxane (5 mL) was stirred at 80 °C for 1 h. The mixture was then cooled to r.t., and the Claycop was collected by filtration and washed with 1,4-dioxane (3 × 5 mL). The organic phases were combined and concentrated under vacuum. The crude product was purified by recrystallization or column chromatography (EtOAc–hexanes) to give a crystalline yellow solid With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in 1,4-dioxane, Time= 1h, T= 80 °C , Green chemistry, stereoselective reaction Begari, Eeshwaraiah; Singh, Chandani; Nookaraju; Kumar, Pradeep; Synlett; vol. 25; nb. 14; (2014); p. 1997 - 2000; Art.No: ST-2014-D0206-L View in Reaxys

62 %

With Iron(III) nitrate nonahydrate, 2,2,6,6-tetramethyl-piperidine-N-oxyl in 1,2-dichloro-ethane, Time= 12h, T= 80 °C , Molecular sieve, stereoselective reaction

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Naveen, Togati; Maity, Soham; Sharma, Upendra; Maiti, Debabrata; Journal of Organic Chemistry; vol. 78; nb. 12; (2013); p. 5949 - 5954 View in Reaxys 49 %

22 :General procedure: The specific procedure was as follows: olefin (0.5 mmol), NH4I (1.5 equiv., 0.75 mmol, 108 mg), TBHP (70percent H2O, 6.0 equiv., 3.0 mmol, 384 mg), TPPFeCl (3-5percent) and acetonitrile) is added to the sealed tube. Add acetonitrile first, then add olefins, NH4I and TPPFeCl, and finally add TBHP. The reaction was vigorously stirred at 120 °C for 6 hours and monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, then filtered and washed with ethyl acetate (EA). Finally, the filtrate was concentrated with a rotary evaporator and purified by column chromatography using silica gel (200-300 mesh sieve) using petroleum ether (PE)/ethyl acetate (EA) as eluant. With tert.-butylhydroperoxide, ammonium iodide, meso-tetraphenylporphyrin iron(III) chloride in water, acetonitrile, Time= 6h, T= 120 °C , Sealed tube Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN106995373; (2017); (A) Chinese View in Reaxys

49 %

22 : Examples 22 to 28 were reacted according to the following reaction scheme General procedure: The pecific steps for the operation are: olefin (0.5 mmol), NH4I (1.5 equivalent, 0.75 mmol, 108 mg), TBHP (70percent of H2O, 6.0 equivalent, 3.0 mmol, 384 mg), TPPFeCl molar amount of 3 - 5percent) and acetonitrile (2 ml) is added to the sealed tube. First add the acetonitrile, then adding olefin, NH4I and TPPFeCl, finally adding TBHP. The reaction in the 120 °C vigorously under stirring 6 hours, and through the TLC monitoring. After the reaction is finished, then cooling the mixture to room temperature, then filtered and ethyl acetate (EA) washing . Finally, the rotary evaporator for concentrating the filtrate, petroleum ether / ethyl acetate (PE) as the eluting agent, the silica gel (200 - 300 mesh sieve) to column chromatographic purification. With tert.-butylhydroperoxide, ammonium iodide, meso-tetraphenylporphyrin iron(III) chloride in water, acetonitrile, Time= 6h, T= 120 °C , Sealed tube, Green chemistry, stereoselective reaction Patent; Yuanjiang Hualong Catalysis Technology Co., Ltd.; Guo Cancheng; Cao Zhongzhong; Guo Xin; (25 pag.); CN107032939; (2017); (A) Chinese View in Reaxys

44 %

With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Time= 6h, Inert atmosphere, Sealed tube, Sonication Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633 View in Reaxys

42 %

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Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585 View in Reaxys Reaction Steps: 2 1: 60percent aq. nitric acid / 0.33 h / 0 °C 2: Et3N / CHCl3 / 3 h / Ambient temperature With nitric acid, triethylamine in chloroform Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys With tetrafluoroboric acid, iodine, copper(II) oxide, sodium nitrite in water, acetonitrile Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys With silver(I) nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in 1,2-dichloro-ethane, Time= 12h, T= 70 °C , Sealed tube, Molecular sieve Andreou, Dimitrios; Kallitsakis, Michael G.; Loukopoulos, Edward; Gabriel, Catherine; Kostakis, George E.; Lykakis, Ioannis N.; Journal of Organic Chemistry; vol. 83; nb. 4; (2018); p. 2104 - 2113 View in Reaxys 3. General procedure for the synthesis of nitroolefins3,4,5 To an oven-dried flask was added AgNO2 (4.5 equiv.), TEMPO (0.6 equiv.), olefin and oven-dried molecular sieves (4 Å, 225 mg). The olefin (if it was liquid) and solvent (DCE, 3 mL) were added by microliter syringe and laboratory syringe respectively. The mixture was stirred for 24 h at room temperature. The reaction mixture was filtered through a celite bed filter using ethyl acetate as the washing solvent. Finally, organic extract was concentrated and was purified by column chromatography using silica gel (200-300/300-400 mesh) and PET-ether/ ethyl acetate as the eluent, and then olefin has been observed. With silver(I) nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, Time= 24h, T= 20 °C , Molecular sieve

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Yuan, Jia-Ni; Liu, Hui-Xia; Tian, Qin-Qin; Ji, Nan; Shen, Kuo; He, Wei; Synthesis (Germany); vol. 50; nb. 13; (2018); p. 2577 - 2586 View in Reaxys O N O O

Rx-ID: 14088088 View in Reaxys 15/140 Yield

Conditions & References Reaction Steps: 2 1: 23 percent / ethylenediamine / acetonitrile / 12 h / Heating 2: 93 percent / m-CPBA / 1,2-dichloro-ethane / 4 h / Heating With ethylenediamine, 3-chloro-benzenecarboperoxoic acid in 1,2-dichloro-ethane, acetonitrile Jang, Yeong-Jiunn; Lin, Wen-Wei; Shih, Yuh-Kuo; Liu, Ju-Tsung; Hwang, Ming-Hsing; Yao, Ching-Fa; Tetrahedron; vol. 59; nb. 27; (2003); p. 4979 - 4992 View in Reaxys

O N N O

Rx-ID: 28714431 View in Reaxys 16/140 Yield

Conditions & References UV-irradiation Toogood, Helen S.; Fryszkowska, Anna; Hare, Victoria; Fisher, Karl; Roujeinikova, Anna; Leys, David; Gardiner, John M.; Stephens, Gill M.; Scrutton, Nigel S.; Advanced Synthesis and Catalysis; vol. 350; nb. 17; (2008); p. 2789 - 2803 View in Reaxys O N O

Rx-ID: 30913585 View in Reaxys 17/140 Yield

Conditions & References Reaction Steps: 2 1: nitric acid / 0.33 h / 0 °C 2: triethylamine / chloroform / 3 h / 20 °C With nitric acid, triethylamine in chloroform Durchschein, Katharina; Fabian, Walter M. F.; MacHeroux, Peter; Zangger, Klaus; Trimmel, Gregor; Faber, Kurt; Organic and Biomolecular Chemistry; vol. 9; nb. 9; (2011); p. 3364 - 3369 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite Xu, Chuanxiang; Xu, Jiaxi; Amino Acids; vol. 41; nb. 1; (2011); p. 195 - 203 View in Reaxys With silver(I) nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in 1,2-dichloro-ethane, Time= 12h, T= 70 °C , Sealed tube, Molecular sieve Li, Jing; Lear, Martin J.; Hayashi, Yujiro; Chemical Communications; vol. 54; nb. 49; (2018); p. 6360 - 6363 View in Reaxys

9/58

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O N O O

Rx-ID: 31039224 View in Reaxys 18/140 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / diethyl ether / 3 h / 0 °C / Inert atmosphere 1.2: Reflux; Inert atmosphere 2.1: tetrafluoroboric acid; iodine; copper(II) oxide; sodium nitrite / water; acetonitrile With tetrafluoroboric acid, n-butyllithium, iodine, copper(II) oxide, sodium nitrite in diethyl ether, water, acetonitrile, 1.2: Wittig reaction Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327 View in Reaxys Reaction Steps: 2 1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform, 1.2: Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 3 1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 60 °C 2: sodium hydroxide / ethanol; water / 60 °C 3: copper(l) chloride; tert.-butylnitrite / acetonitrile / 80 °C With tert.-butylnitrite, sodium hydride, copper(l) chloride, sodium hydroxide in tetrahydrofuran, ethanol, water, acetonitrile, mineral oil Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys Reaction Steps: 3 1: potassium tert-butylate / tetrahydrofuran 2: nitric acid / water 3: sodium hydroxide / water; dichloromethane With potassium tert-butylate, nitric acid, sodium hydroxide in tetrahydrofuran, dichloromethane, water, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube

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With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O O

Rx-ID: 35500904 View in Reaxys 19/140 Yield

Conditions & References

88 %

Synthesis of trans-β-Nitroalkenes General procedure: Method A: An aromatic aldehyde (0.05 M) was dropped into a solution of ammonium acetate (0.012 M) in dry nitromethane (10 mL) and acetic acid (20 mL) at 90 °C with stirring. Then the mixture was heated at reflux for 5 h, after that the mixture was poured into water and extracted with ethyl acetate (3×50 mL). The extracts were washed with saturated NaCl solution and dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was recrystallized from methanol or purified by column chromatography on silica gel [ethyl acetate/petroleum ether] to afford the target trans-α-nitroalkenes. With ammonium acetate in acetic acid, Time= 5h, T= 90 °C , Reflux Xu, Changzhu; Du, Jianguo; Ma, Lichao; Li, Guowei; Tao, Minli; Zhang, Wenqin; Tetrahedron; vol. 69; nb. 23; (2013); p. 4749 - 4757 View in Reaxys O N

Rx-ID: 36370061 View in Reaxys 20/140 Yield

Conditions & References

71%

With tert.-butylnitrite, copper(l) chloride in acetonitrile, T= 80 °C Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys O

O N O

Rx-ID: 36370089 View in Reaxys 21/140 Yield

Conditions & References Reaction Steps: 2 1: sodium hydroxide / ethanol; water / 60 °C 2: copper(l) chloride; tert.-butylnitrite / acetonitrile / 80 °C With tert.-butylnitrite, copper(l) chloride, sodium hydroxide in ethanol, water, acetonitrile Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys

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O N O

Rx-ID: 38200009 View in Reaxys 22/140 Yield

Conditions & References With silver(I) nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in 1,2-dichloro-ethane, T= 70 °C Wu, Na; Wahl, Benoit; Woodward, Simon; Lewis, William; Chemistry - A European Journal; vol. 20; nb. 25; (2014); p. 7718 - 7724 View in Reaxys O N O

Rx-ID: 975908 View in Reaxys 23/140 Yield

Conditions & References With diethyl ether, nitrosylchloride Ogloblin,K.A. et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 34; (1964); p. 170 - 181,168 - 178 View in Reaxys

N O

Rx-ID: 2056444 View in Reaxys 24/140 Yield

Conditions & References With iodine, dinitrogen tetraoxide, triethylamine, 1.) ether, 0 deg C, 0.5 h, 2.) ether, RT, 5 h, Yield given. Multistep reaction Grant, Richard D.; Pinhey, John T.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1231 - 1244 View in Reaxys Reaction Steps: 2 1: nitric acid; sulfuric acid / 0.33 h / 0 °C 2: 49 percent / triethylamine / CHCl3 / Heating With sulfuric acid, nitric acid, triethylamine in chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys O N O

Rx-ID: 7560614 View in Reaxys 25/140 Yield

Conditions & References α,α-Dimethylstyrol, NO, CCl4 (RT, Sonnenlicht) Tuaillon; Perrot; Helvetica Chimica Acta; vol. 61; (1978); p. 558,563 View in Reaxys

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O O

N O

Rx-ID: 8839943 View in Reaxys 26/140 Yield

Conditions & References

49 %, 14 %

With triethylamine in chloroform, Heating Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys O N

O N O

Rx-ID: 11138675 View in Reaxys 27/140 Yield

Conditions & References With N-butylamine in toluene, Heating Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977 View in Reaxys O O

N O

Rx-ID: 11163862 View in Reaxys 28/140 Yield

Conditions & References Stage 1: With nitric acid, acetic anhydride Stage 2: With triethylamine in chloroform, Further stages. Title compound not separated from byproducts. Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys With silver(I) nitrite in 1,2-dichloro-ethane, T= 80 Â°C , Sealed tube, Inert atmosphere, Molecular sieve Manna, Srimanta; Antonchick, Andrey P.; Chemistry - A European Journal; vol. 23; nb. 32; (2017); p. 7825 - 7829 View in Reaxys O N O

Rx-ID: 11371875 View in Reaxys 29/140

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Yield

Conditions & References Reaction Steps: 2 1.1: p-CH3C6H4SO3H*H2O / toluene / 2 h / Heating 2.1: Ac2O; conc. HNO3 2.2: Et3N / CHCl3 With nitric acid, acetic anhydride, toluene-4-sulfonic acid in toluene Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys O N O

Rx-ID: 11382620 View in Reaxys 30/140 Yield

Conditions & References Reaction Steps: 3 1.1: Mg / diethyl ether 1.2: diethyl ether / 6 h / 20 °C 2.1: p-CH3C6H4SO3H*H2O / toluene / 2 h / Heating 3.1: Ac2O; conc. HNO3 3.2: Et3N / CHCl3 With nitric acid, acetic anhydride, toluene-4-sulfonic acid, magnesium in diethyl ether, toluene, 1.2: Grignard reaction Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys Reaction Steps: 2 1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform, 1.2: Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 3 1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 60 °C 2: sodium hydroxide / ethanol; water / 60 °C 3: copper(l) chloride; tert.-butylnitrite / acetonitrile / 80 °C With tert.-butylnitrite, sodium hydride, copper(l) chloride, sodium hydroxide in tetrahydrofuran, ethanol, water, acetonitrile, mineral oil Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys

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Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O

Rx-ID: 15341162 View in Reaxys 31/140 Yield

Conditions & References Reaction Steps: 2 1: nitric acid; sulfuric acid / 0.33 h / 0 °C 2: 14 percent / triethylamine / CHCl3 / Heating With sulfuric acid, nitric acid, triethylamine in chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

(CH3(CH2)3)3ZnLi O

N O

Rx-ID: 15350784 View in Reaxys 32/140 Yield

Conditions & References Reaction Steps: 3 1: 62 percent / butyllithium / diethyl ether; hexane / Heating 2: nitric acid; sulfuric acid / 0.33 h / 0 °C 3: 49 percent / triethylamine / CHCl3 / Heating With n-butyllithium, sulfuric acid, nitric acid, triethylamine in diethyl ether, hexane, chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys O N O

(CH3(CH2)3)3ZnLi O

Rx-ID: 15350788 View in Reaxys 33/140 Yield

Conditions & References Reaction Steps: 3 1: 62 percent / butyllithium / diethyl ether; hexane / Heating 2: nitric acid; sulfuric acid / 0.33 h / 0 °C 3: 14 percent / triethylamine / CHCl3 / Heating With n-butyllithium, sulfuric acid, nitric acid, triethylamine in diethyl ether, hexane, chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

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O N O

Rx-ID: 33798397 View in Reaxys 34/140 Yield 52 %

Conditions & References With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sealed tube, Sonication Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O

Rx-ID: 33798419 View in Reaxys 35/140 Yield 26 %

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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O N O

Rx-ID: 33798506 View in Reaxys 36/140 Yield

Rx-ID: 36370062 View in Reaxys 37/140 Yield

Conditions & References

70%

N O

Rx-ID: 36370090 View in Reaxys 38/140 Yield

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View in Reaxys O N O

Rx-ID: 44831195 View in Reaxys 39/140 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O

Rx-ID: 44831197 View in Reaxys 40/140 Yield

Conditions & References With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O

Rx-ID: 45328030 View in Reaxys 41/140 Yield 41 %

Conditions & References Typical Procedure General procedure: The mixture of α,α-Unsaturated Acids (0.5 mmol), Fe(NO3)3 (1.0 mmol), Pyridine (0.5 mmol) and toluene (2 ml) was stirred at 100 °C for 12 h. After cooling to r.t., the reaction mixture was washed with H2O (10 ml), and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (EA/n-Hexane=15percent) to afford pure product. With pyridine, Iron(III) nitrate nonahydrate in toluene, Time= 12h, T= 100 °C Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 - 1082; Art.No: ST-2016-W0789-L View in Reaxys

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O O

N O

Rx-ID: 45473912 View in Reaxys 42/140 Yield

Conditions & References Reaction Steps: 2 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chlorobenzene / 6 h / 110 - 120 °C / Sealed tube; Inert atmosphere 2: silver(I) nitrite / 1,2-dichloro-ethane / 80 °C / Sealed tube; Inert atmosphere; Molecular sieve With silver(I) nitrite, 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2-dichloro-ethane, chlorobenzene Manna, Srimanta; Antonchick, Andrey P.; Chemistry - A European Journal; vol. 23; nb. 32; (2017); p. 7825 - 7829 View in Reaxys O

O O

N O

O F

Rx-ID: 11138690 View in Reaxys 43/140 Yield

Conditions & References With triethylamine in chloroform, T= 20 °C Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977 View in Reaxys With sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys O N O F

Rx-ID: 11418829 View in Reaxys 44/140 Yield 35 %

18 %

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1: nitric acid / 3 h / 0 °C 2: triethylamine / CHCl3 / 20 °C With nitric acid, triethylamine in chloroform Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977 View in Reaxys With tetrafluoroboric acid, iodine, copper(II) oxide, sodium nitrite in water, acetonitrile Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys O F

N O

Rx-ID: 33798453 View in Reaxys 45/140 Yield

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O N O F O

Rx-ID: 33798488 View in Reaxys 46/140 Yield

N O

Rx-ID: 33798509 View in Reaxys 47/140 Yield

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O N

F F

Rx-ID: 36064904 View in Reaxys 48/140 Yield

Conditions & References

28 %

F F

Rx-ID: 41747024 View in Reaxys 49/140 Yield

O N

Rx-ID: 3923406 View in Reaxys 50/140 Yield 8 %, 33 %

Conditions & References With n-Amyl nitrite, acetic acid, Time= 0.5h, Heating Yandovskii, V. N.; Ryabinkin, I. I.; Tselinskii, I. V.; Journal of Organic Chemistry USSR (English Translation); vol. 16; nb. 10; (1980); p. 1773 - 1775; Zhurnal Organicheskoi Khimii; vol. 16; nb. 10; (1980); p. 2084 - 2086 View in Reaxys

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O N O

O N

N O

Rx-ID: 11138676 View in Reaxys 51/140 Yield

Rx-ID: 31039196 View in Reaxys 52/140 Yield

Conditions & References With tetrafluoroboric acid, iodine, copper(II) oxide, sodium nitrite in water, acetonitrile Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys O N O N

Rx-ID: 31039199 View in Reaxys 53/140 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / diethyl ether / 3 h / 0 Â°C / Inert atmosphere 1.2: Reflux; Inert atmosphere 2.1: tetrafluoroboric acid; iodine; copper(II) oxide; sodium nitrite / water; acetonitrile With tetrafluoroboric acid, n-butyllithium, iodine, copper(II) oxide, sodium nitrite in diethyl ether, water, acetonitrile, 1.2: Wittig reaction Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan; Organic and Biomolecular Chemistry; vol. 9; nb. 11; (2011); p. 4323 - 4327 View in Reaxys

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O N O

Rx-ID: 33798403 View in Reaxys 54/140 Yield

Rx-ID: 33798448 View in Reaxys 55/140 Yield

O N

N O

Rx-ID: 4535440 View in Reaxys 56/140 Yield 20 %

Conditions & References With N,N-diethylethylenediamine in benzene, Time= 72h, Heating Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288 View in Reaxys O N O O

Rx-ID: 11163844 View in Reaxys 57/140

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Yield 39 %

31 %

Stage 1: With nitric acid, acetic anhydride Stage 2: With triethylamine in chloroform, Further stages. Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O O HO

Rx-ID: 11373544 View in Reaxys 58/140 Yield

Conditions & References Reaction Steps: 2 1.1: p-CH3C6H4SO3H*H2O / toluene / 2 h / Heating 2.1: Ac2O; conc. HNO3 2.2: 3 percent / Et3N / CHCl3 With nitric acid, acetic anhydride, toluene-4-sulfonic acid in toluene Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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O N O O O

Rx-ID: 11384992 View in Reaxys 59/140 Yield

Conditions & References Reaction Steps: 3 1.1: Mg / diethyl ether 1.2: diethyl ether / 6 h / 20 °C 2.1: p-CH3C6H4SO3H*H2O / toluene / 2 h / Heating 3.1: Ac2O; conc. HNO3 3.2: 3 percent / Et3N / CHCl3 With nitric acid, acetic anhydride, toluene-4-sulfonic acid, magnesium in diethyl ether, toluene, 1.2: Grignard reaction Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys Reaction Steps: 2 1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform, 1.2: Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 3 1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 60 °C 2: sodium hydroxide / ethanol; water / 60 °C 3: copper(l) chloride; tert.-butylnitrite / acetonitrile / 80 °C With tert.-butylnitrite, sodium hydride, copper(l) chloride, sodium hydroxide in tetrahydrofuran, ethanol, water, acetonitrile, mineral oil Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys Reaction Steps: 3 1: potassium tert-butylate / tetrahydrofuran 2: nitric acid / water 3: sodium hydroxide / water; dichloromethane With potassium tert-butylate, nitric acid, sodium hydroxide in tetrahydrofuran, dichloromethane, water, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere

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2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O O

N O

Rx-ID: 27925393 View in Reaxys 60/140 Yield 40 %

Conditions & References With ammonium cerium(IV) nitrate, acetic acid, sodium nitrite in chloroform, sonication Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O O

N O

Rx-ID: 27925394 View in Reaxys 61/140 Yield 47 %

Conditions & References With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Time= 6h, Inert atmosphere, Sealed tube, Sonication Trost, Barry M.; Bringley, Dustin A.; O'Keefe, B. Michael; Organic Letters; vol. 15; nb. 22; (2013); p. 5630 - 5633 View in Reaxys

40 %

33 %

With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sealed tube, Sonication

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Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O

Rx-ID: 36370063 View in Reaxys 62/140 Yield

Conditions & References

52%

Rx-ID: 36370091 View in Reaxys 63/140 Yield

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Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys O O

Rx-ID: 41747022 View in Reaxys 64/140 Yield

Conditions & References Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys Reaction Steps: 2 1: potassium tert-butylate / tetrahydrofuran 2: ammonium cerium (IV) nitrate; sodium nitrite; acetic acid / chloroform With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys O O

N O

O O

Rx-ID: 41958465 View in Reaxys 65/140 Yield

Conditions & References Reaction Steps: 3 1: potassium tert-butylate / tetrahydrofuran 2: nitric acid / water 3: sodium hydroxide / water; dichloromethane With potassium tert-butylate, nitric acid, sodium hydroxide in tetrahydrofuran, dichloromethane, water, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys

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O O

N O

Rx-ID: 41958508 View in Reaxys 66/140 Yield

Conditions & References With sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys

O O

N O

N O O O

Rx-ID: 41958511 View in Reaxys 67/140 Yield

N O

Rx-ID: 45328037 View in Reaxys 68/140 Yield 38 %

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N O

Cl O

Rx-ID: 2846395 View in Reaxys 69/140 Yield

Conditions & References

73 %

With sodium hydroxide in chloroform, Time= 24h, T= 22 °C Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585 View in Reaxys With triethylamine in chloroform, Time= 3h, Ambient temperature Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys With triethylamine in chloroform, T= 20 °C Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977 View in Reaxys O

Rx-ID: 11138677 View in Reaxys 70/140 Yield

Rx-ID: 11163860 View in Reaxys 71/140 Yield

Cl HO Cl

Rx-ID: 11371985 View in Reaxys 72/140

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Yield

Cl O Cl

Rx-ID: 11378478 View in Reaxys 73/140 Yield

Conditions & References Reaction Steps: 3 1.1: Mg / diethyl ether 1.2: diethyl ether / 6 h / 20 °C 2.1: p-CH3C6H4SO3H*H2O / toluene / 2 h / Heating 3.1: Ac2O; conc. HNO3 3.2: Et3N / CHCl3 With nitric acid, acetic anhydride, toluene-4-sulfonic acid, magnesium in diethyl ether, toluene, 1.2: Grignard reaction Zagozda, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 18; nb. 12; (2007); p. 1457 - 1464 View in Reaxys Reaction Steps: 2 1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform, 1.2: Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys Reaction Steps: 3 1: potassium tert-butylate / tetrahydrofuran 2: nitric acid / water 3: sodium hydroxide / water; dichloromethane With potassium tert-butylate, nitric acid, sodium hydroxide in tetrahydrofuran, dichloromethane, water, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube

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Rx-ID: 11417582 View in Reaxys 74/140 Yield 56 %

50 %

38 %

With ammonium cerium(IV) nitrate, acetic acid, sodium nitrite in chloroform, sonication Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys Reaction Steps: 2 1: nitric acid / 3 h / 0 °C 2: triethylamine / CHCl3 / 20 °C With nitric acid, triethylamine in chloroform Martin, Nolwenn J. A.; Ozores, Lidia; List, Benjamin; Journal of the American Chemical Society; vol. 129; nb. 29; (2007); p. 8976 - 8977 View in Reaxys Reaction Steps: 2 1: 83 percent / aq. nitric acid / 0.17 h / -20 - -10 °C 2: 73 percent / aq. NaOH / CHCl3 / 24 h / 22 °C With sodium hydroxide, nitric acid in chloroform Wu, Jing; Mampreian, Dawn M.; Hoveyda, Amir H.; Journal of the American Chemical Society; vol. 127; nb. 13; (2005); p. 4584 - 4585 View in Reaxys Reaction Steps: 2 1: 60percent aq. nitric acid / 0.33 h / 0 °C 2: Et3N / CHCl3 / 3 h / Ambient temperature With nitric acid, triethylamine in chloroform Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate

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Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N

6-<p-tolylimino-methyl>-benzo<1.3>dioxol-5-ylamine

O Cl

Rx-ID: 20517804 View in Reaxys 75/140 Yield

Conditions & References Reaction Steps: 3 1: 1.) BuLi / 1.) Et2O, hexane, 4 h, 2.) reflux, overnight 2: 60percent aq. nitric acid / 0.33 h / 0 Â°C 3: Et3N / CHCl3 / 3 h / Ambient temperature With n-butyllithium, nitric acid, triethylamine in chloroform Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys O N O

Cl N

O Cl

Rx-ID: 27925395 View in Reaxys 76/140 Yield

Conditions & References in ethanol, UV-irradiation Fryszkowska, Anna; Fisher, Karl; Gardiner, John M.; Stephens, Gill M.; Journal of Organic Chemistry; vol. 73; nb. 11; (2008); p. 4295 - 4298 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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N O

Rx-ID: 33798464 View in Reaxys 77/140 Yield 72 %

Conditions & References 1 : Preparation of (E)-1 -chloro-3-(1 -n itroprop-1 -en-2-yl)benzene from 1-chloro-3-(prop-1 -en-2-yl)benzene Starting material 1-chloro-3-(prop-1-en-2-yl) (23 mmol; 3.5 g) was dissolved in chloroform (80 mL) in a 250 mL flask equipped with a magnetic stir bar. Afterwards sodium nitrite (230 mmol; 15.9 g) and cerium(IV) ammonium nitrate (CAN; 23 mmol; 12.6 g) were added and the reaction mixture was vigorously stirred for 15 minutes. Acetic acid (276 mmol; 15.8 mL) was then slowly added drop wise (60 mm) and the reaction system was intensively stirred at 30 °C until TLC showed total consumption of starting material. After the completion of the reaction, the reaction mixture was filtered, the solvent was evaporated under reduced pressure, the organic residue was diluted with water and neutralized with a saturated solution of NaHCO3. The aqueous layer was extracted with EtOAc (3 x 100 mL), the organic phases were washed with brine and dried under Na2SO4. After evaporation of the solvent under reduced pressure, the crude product was obtained which was purified with flash column chromatograph (Si02 n-hexane-EtOAc = 10: 1) to afford yellow solid product (6.2 g, 72percent yield).NMR (500 MHz, ODd3, ppm) 6 7.45-7.30 (m, 4ArH), 7.24 (m, 1 H), 2.65 (m, 3H);NMR (125 MHz, ODd3, ppm) 6 148.2, 140.1, 136.9, 135.5, 130.4, 126.4, 125.0,18.5. Stage 1: With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Time= 0.25h Stage 2: With acetic acid in chloroform, T= 30 °C Patent; LEK PHARMACEUTICALS D.D.; STAVBER, Gaj; GAZIC SMILOVIC, Ivana; CLUZEAU, Jerome; RICHTER, Frank; WO2014/202765; (2014); (A1) English View in Reaxys

63 %

With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sealed tube, Sonication Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Rubén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. 24; (2016); p. 4049 - 4056 View in Reaxys

43 %

With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sealed tube, Sonication Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube

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Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O

N O

Rx-ID: 33798498 View in Reaxys 78/140 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform, 1.2: Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys Reaction Steps: 2 1: potassium tert-butylate / tetrahydrofuran 2: ammonium cerium (IV) nitrate; sodium nitrite; acetic acid / chloroform With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys Reaction Steps: 2 1.1: n-butyllithium / diethyl ether / 1 h / Inert atmosphere 1.2: 24 h / 20 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sealed tube; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, chloroform Gini, Andrea; Bamberger, Julia; Luis-Barrera, Javier; Zurro, Mercedes; Mas-Ballesté, Rubén; Alemán, José; Mancheño, Olga García; Advanced Synthesis and Catalysis; vol. 358; nb. 24; (2016); p. 4049 - 4056 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys

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O N O

N O

Rx-ID: 35656665 View in Reaxys 79/140 Yield

Conditions & References With tetrakis(triphenylphosphine) palladium(0), copper(I) thiophene-2-carboxylate in methanol, Time= 2h, T= 22 Â°C , chemoselective reaction

90 %

Creech, Gardner S.; Kwon, Ohyun; Chemical Science; vol. 4; nb. 6; (2013); p. 2670 - 2674 View in Reaxys O N

Rx-ID: 36064908 View in Reaxys 80/140 Yield

Conditions & References With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys O N

Rx-ID: 41958453 View in Reaxys 81/140 Yield

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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O N O

Cl O

Rx-ID: 41958460 View in Reaxys 82/140 Yield

Rx-ID: 41958483 View in Reaxys 83/140 Yield

Conditions & References Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys O

O Cl

N O

Rx-ID: 41958501 View in Reaxys 84/140 Yield

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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N O

Cl N

Rx-ID: 41958503 View in Reaxys 85/140 Yield

N O

Rx-ID: 30116320 View in Reaxys 86/140 Yield

Conditions & References

54 %Spectr., 9 %Spectr.

With Iron(III) nitrate nonahydrate, lithium chloride in acetonitrile, Time= 5h, Reflux, Inert atmosphere Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132 View in Reaxys

O O

N N

Rx-ID: 4531880 View in Reaxys 87/140 Yield 15 %

Conditions & References With N,N-diethylethylenediamine in benzene, Time= 90h, Heating Barco, Achille; Benetti, Simonetta; De Risi, Carmela; Morelli, Carlo F.; Pollini, Gian P.; Zanirato, Vinicio; Tetrahedron; vol. 52; nb. 27; (1996); p. 9275 - 9288 View in Reaxys O N

O N

O O

N O

Rx-ID: 42311717 View in Reaxys 88/140 Yield

Conditions & References With ammonium cerium (IV) nitrate, sodium nitrite in chloroform, Schlenk technique, Inert atmosphere, Sonication Yu, Yan-Bo; Cheng, Lei; Li, Yi-Pan; Fu, Yue; Zhu, Shou-Fei; Zhou, Qi-Lin; Chemical Communications; vol. 52; nb. 26; (2016); p. 4812 - 4815 View in Reaxys

Copyright ÂŠ 2018 Elsevier Life Sciences IP Limited except certain content provided by third parties. Reaxys is a trademark of Elsevier Life Sciences IP Limited.

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Rx-ID: 4033060 View in Reaxys 89/140 Yield

Conditions & References With hydrogenchloride, sodium nitrite in tetrachloromethane, water, Time= 1.5h, T= 0 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p. 1441 1452 View in Reaxys With hydrogenchloride, sodium nitrite in tetrachloromethane, water, Time= 1.5h, T= 0 °C , Yields of byproduct given. Title compound not separated from byproducts Abbenante, Giovanni; Hughes, Robert; Prager, Rolf H.; Australian Journal of Chemistry; vol. 47; nb. 8; (1994); p. 1441 1452 View in Reaxys O

O Cl O

N Cl

Rx-ID: 8841047 View in Reaxys 90/140 Yield

Conditions & References

37 %

With triethylamine in chloroform, Heating Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys O Cl O

N O

Rx-ID: 8841133 View in Reaxys 91/140 Yield 34 %

Conditions & References With triethylamine in chloroform, Heating Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

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Cl O

N O

Rx-ID: 8841134 View in Reaxys 92/140 Yield

Conditions & References

43 %

With triethylamine in chloroform, Heating Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys Cl Cl

N O

Rx-ID: 15339963 View in Reaxys 93/140 Yield

Conditions & References Reaction Steps: 3 1: 56 percent / butyllithium / diethyl ether; hexane / Heating 2: nitric acid; sulfuric acid / 0.33 h / 0 °C 3: 43 percent / triethylamine / CHCl3 / Heating With n-butyllithium, sulfuric acid, nitric acid, triethylamine in diethyl ether, hexane, chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

N Cl

Rx-ID: 15342435 View in Reaxys 94/140 Yield

Conditions & References Reaction Steps: 2 1: nitric acid; sulfuric acid / 0.33 h / 0 °C 2: 37 percent / triethylamine / CHCl3 / Heating With sulfuric acid, nitric acid, triethylamine in chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

Cl N

O Cl

Rx-ID: 15345899 View in Reaxys 95/140 Yield

Conditions & References Reaction Steps: 3 1: 52 percent / butyllithium / diethyl ether; hexane / Heating 2: nitric acid; sulfuric acid / 0.33 h / 0 °C 3: 37 percent / triethylamine / CHCl3 / Heating With n-butyllithium, sulfuric acid, nitric acid, triethylamine in diethyl ether, hexane, chloroform

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Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

N O

Rx-ID: 15351740 View in Reaxys 96/140 Yield

Conditions & References Reaction Steps: 3 1: 56 percent / butyllithium / diethyl ether; hexane / Heating 2: nitric acid; sulfuric acid / 0.33 h / 0 °C 3: 34 percent / triethylamine / CHCl3 / Heating With n-butyllithium, sulfuric acid, nitric acid, triethylamine in diethyl ether, hexane, chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys

N O

Rx-ID: 15359847 View in Reaxys 97/140 Yield

Conditions & References Reaction Steps: 2 1: nitric acid; sulfuric acid / 0.33 h / 0 °C 2: 34 percent / triethylamine / CHCl3 / Heating With sulfuric acid, nitric acid, triethylamine in chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys Cl

N O

Rx-ID: 15359850 View in Reaxys 98/140 Yield

Conditions & References Reaction Steps: 2 1: nitric acid; sulfuric acid / 0.33 h / 0 °C 2: 43 percent / triethylamine / CHCl3 / Heating With sulfuric acid, nitric acid, triethylamine in chloroform Kawai, Yasushi; Inaba, Yoshikazu; Tokitoh, Norihiro; Tetrahedron Asymmetry; vol. 12; nb. 2; (2001); p. 309 - 318 View in Reaxys O

N O

F O

F F

Rx-ID: 44831256 View in Reaxys 99/140

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Yield

N O

F F

Rx-ID: 44831262 View in Reaxys 100/140 Yield

Rx-ID: 33798411 View in Reaxys 101/140 Yield

Rx-ID: 33798443 View in Reaxys 102/140 Yield

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Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys O N O

Rx-ID: 41746872 View in Reaxys 103/140 Yield

Conditions & References

45 %

Rx-ID: 41747006 View in Reaxys 104/140 Yield

O O

Rx-ID: 42311710 View in Reaxys 105/140 Yield

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O O

N O

Rx-ID: 29723952 View in Reaxys 106/140 Yield

Conditions & References

9 %, 15 %

With palladium(II) trifluoroacetate, dimethyl sulfoxide, silver carbonate in 1,4-dioxane, Time= 24h, T= 100 °C , Inert atmosphere, optical yield given as percent de Zhang, Min; Zhou, Jun; Kan, Jian; Wang, Min; Su, Weiping; Hong, Maochun; Chemical Communications; vol. 46; nb. 30; (2010); p. 5455 - 5457 View in Reaxys O N O

F F F

Rx-ID: 7604150 View in Reaxys 107/140 Yield

Conditions & References entspr. Styrol mit HNO3 Patent; Procter + Gamble; US3584056; (1971); ; vol. 75; nb. 48419 View in Reaxys O N O

F F F

Rx-ID: 33798445 View in Reaxys 108/140 Yield

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View in Reaxys O N O

F F

Rx-ID: 33798472 View in Reaxys 109/140 Yield

Conditions & References With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N O

F F F

Rx-ID: 33798484 View in Reaxys 110/140 Yield

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O N O

F F O F

F F

Rx-ID: 33798501 View in Reaxys 111/140 Yield

O O

O N

N O O

Rx-ID: 401208 View in Reaxys 112/140 Yield

Conditions & References Clayton; Journal of the Chemical Society; vol. 97; (1910); p. 1407 View in Reaxys O O

O O

O N

Rx-ID: 401209 View in Reaxys 113/140 Yield

Conditions & References With sodium hydroxide Clayton; Journal of the Chemical Society; vol. 97; (1910); p. 1407 View in Reaxys

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O O

N O

Rx-ID: 22325511 View in Reaxys 114/140 Yield

Conditions & References Reaction Steps: 2 1: HNO3+H2SO4 2: NaOH-solution With sodium hydroxide, sulfuric acid, nitric acid Clayton; Journal of the Chemical Society; vol. 97; (1910); p. 1407 View in Reaxys O

N O

Br O

Rx-ID: 2846396 View in Reaxys 115/140 Yield

Conditions & References With triethylamine in chloroform, Time= 3h, Ambient temperature Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys O N O

Rx-ID: 20510642 View in Reaxys 116/140 Yield 41 %

27 %

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Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys With ammonium cerium (IV) nitrate Li, Shengkun; Huang, Kexuan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Chemistry - A European Journal; vol. 19; nb. 33; (2013); p. 10840 - 10844 View in Reaxys With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Sonication, Sealed tube Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O N

HNO3+H2SO4

O Br

Rx-ID: 20517808 View in Reaxys 117/140 Yield

Conditions & References Reaction Steps: 3 1: 1.) BuLi / 1.) Et2O, hexane, 4 h, 2.) reflux, overnight 2: 60percent aq. nitric acid / 0.33 h / 0 °C 3: Et3N / CHCl3 / 3 h / Ambient temperature With n-butyllithium, nitric acid, triethylamine in chloroform Ohta, Hiromichi; Kobayashi, Naoki; Ozaki, Kazuhiko; Journal of Organic Chemistry; vol. 54; nb. 8; (1989); p. 1802 - 1804 View in Reaxys

Br N N

Rx-ID: 28714434 View in Reaxys 118/140 Yield

Br N O

Rx-ID: 33798456 View in Reaxys 119/140 Yield

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Br N O

Rx-ID: 33798459 View in Reaxys 120/140 Yield

Br Br

N O

Rx-ID: 33798469 View in Reaxys 121/140 Yield

Br O Br

Rx-ID: 33798490 View in Reaxys 122/140 Yield

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View in Reaxys Reaction Steps: 3 1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 60 °C 2: sodium hydroxide / ethanol; water / 60 °C 3: copper(l) chloride; tert.-butylnitrite / acetonitrile / 80 °C With tert.-butylnitrite, sodium hydride, copper(l) chloride, sodium hydroxide in tetrahydrofuran, ethanol, water, acetonitrile, mineral oil Rokade, Balaji V.; Prabhu, Kandikere Ramaiah; Organic and Biomolecular Chemistry; vol. 11; nb. 39; (2013); p. 6713 6716 View in Reaxys Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Sealed tube; Sonication With ammonium cerium (IV) nitrate, potassium tert-butylate, acetic acid, sodium nitrite in tetrahydrofuran, chloroform Liu, Man; Kong, Duanyang; Li, Meina; Zi, Guofu; Hou, Guohua; Advanced Synthesis and Catalysis; vol. 357; nb. 18; (2015); p. 3875 - 3879 View in Reaxys Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 25 h / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite; ammonium cerium (IV) nitrate / chloroform / Sonication; Sealed tube With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform Sim, Jae Hun; Song, Choong Eui; Angewandte Chemie - International Edition; vol. 56; nb. 7; (2017); p. 1835 - 1839; Angew. Chem.; vol. 129; nb. 7; (2017); p. 1861 - 1865,5 View in Reaxys O

Br Br

N O

Rx-ID: 33798495 View in Reaxys 123/140 Yield

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Rx-ID: 36370064 View in Reaxys 124/140 Yield

Conditions & References

54%

N O

Rx-ID: 36370093 View in Reaxys 125/140 Yield

O N O

Rx-ID: 35468981 View in Reaxys 126/140 Yield

Conditions & References Reaction Steps: 2 1.1: caesium carbonate / 1,2-dimethoxyethane / 5 h / 20 °C / Inert atmosphere 2.1: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,2-dimethoxyethane / 0.17 h / 20 °C / Inert atmosphere 2.2: 5 h / Reflux With palladium diacetate, caesium carbonate, 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl in 1,2-dimethoxyethane Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3194 - 3198 View in Reaxys

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O S O

N O

O N O

Rx-ID: 35469029 View in Reaxys 127/140 Yield

Conditions & References

154 mg

A representative synthetic procedure of skeleton 4 or 6 is as follows: General procedure: Cs2CO3 (652 mg, 2.0 mmol) was added to a solution of skeleton 2 or 5 (1.0 mmol) in dimethoxyethane (DME, 10 mL) at rt. Then triflic anhydride (Tf2O, 290 mg, 1.03 mmol) was slowly added to the reaction mixture. The reaction mixture was stirred at rt for 5 h. The reaction was traced by TLC until skeleton 2 or 5 was consumed. Next, Pd(OAc)2 (34 mg, 0.15 mmol) and racemic BINAP (100 mg, 0.16 mmol) were added to the stirred solution at rt for 10 min. Then NaNO2 (280 mg, 5.0 mmol) and TBAB (322 mg, 1.0 mmol) were added to the reaction mixture. The reaction mixture was stirred at reflux for 5 h. The reaction mixture was cooled to rt. NH4Cl (aq) (1 N, 5 mL) was added to the reaction mixture and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture wasextracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc = 20/1~6/1) afforded skeleton 4 or 6. Stage 1: With palladium diacetate, 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl in 1,2-dimethoxyethane, Time= 0.166667h, T= 20 °C , Inert atmosphere Stage 2: With tetrabutylammomium bromide, sodium nitrite in 1,2-dimethoxyethane, Time= 5h, Reflux Chang, Meng-Yang; Lin, Chung-Han; Tai, Hang-Yi; Tetrahedron Letters; vol. 54; nb. 24; (2013); p. 3194 - 3198 View in Reaxys O N O

O O O O

Rx-ID: 44831181 View in Reaxys 128/140 Yield

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O N O O

Rx-ID: 44831187 View in Reaxys 129/140 Yield

N O

O Cl

Rx-ID: 30116302 View in Reaxys 130/140 Yield

Conditions & References

8 %Spectr., With Iron(III) nitrate nonahydrate, iron(III) chloride in acetonitrile, Time= 0.5h, Reflux, Inert atmosphere 49 %Spectr. Taniguchi, Tsuyoshi; Fujii, Tatsuya; Ishibashi, Hiroyuki; Journal of Organic Chemistry; vol. 75; nb. 23; (2010); p. 8126 8132 View in Reaxys O N O

I O I

Rx-ID: 33798439 View in Reaxys 131/140 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / diethyl ether; hexane / 1 h / Inert atmosphere 1.2: 24 h / 20 Â°C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate; acetic acid; sodium nitrite / chloroform / Inert atmosphere; Sonication With n-butyllithium, ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in diethyl ether, hexane, chloroform, 1.2: Wittig reaction Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 3 1: potassium tert-butylate / tetrahydrofuran 2: nitric acid / water 3: sodium hydroxide / water; dichloromethane With potassium tert-butylate, nitric acid, sodium hydroxide in tetrahydrofuran, dichloromethane, water, 1: |Wittig Olefination Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys

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O N O

Rx-ID: 33798481 View in Reaxys 132/140 Yield

Conditions & References With ammonium cerium (IV) nitrate, acetic acid, sodium nitrite in chloroform, Inert atmosphere, Sonication Li, Shengkun; Huang, Kexuan; Cao, Bonan; Zhang, Jiwen; Wu, Wenjun; Zhang, Xumu; Angewandte Chemie - International Edition; vol. 51; nb. 34; (2012); p. 8573 - 8576 View in Reaxys Reaction Steps: 2 1: nitric acid / water 2: sodium hydroxide / water; dichloromethane With nitric acid, sodium hydroxide in dichloromethane, water Bertolotti, Mattia; Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara; ChemCatChem; vol. 8; nb. 3; (2016); p. 577 - 583 View in Reaxys

O O

N O

N O I I

Rx-ID: 41958504 View in Reaxys 133/140 Yield

O O

N O

O N

OH N O

Rx-ID: 525886 View in Reaxys 134/140 Yield

Conditions & References With alkali Jordan; Thorpe; Journal of the Chemical Society; vol. 107; (1915); p. 401 View in Reaxys

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O O

N O

alkali O

O N

OH N O

Rx-ID: 5567999 View in Reaxys 135/140 Yield

Conditions & References Jordan; Thorpe; Journal of the Chemical Society; vol. 107; (1915); p. 401 View in Reaxys O N O

N O

OH N O

Rx-ID: 22327085 View in Reaxys 136/140 Yield

Conditions & References Reaction Steps: 2 1: HNO3+H2SO4 / 20 °C 2: alkali With sulfuric acid, nitric acid Jordan; Thorpe; Journal of the Chemical Society; vol. 107; (1915); p. 401 View in Reaxys O N O

N HO

OH N O

Rx-ID: 22346305 View in Reaxys 137/140 Yield

Conditions & References Reaction Steps: 3 1: beim Erhitzen ueber den Schmelzpunkt 2: HNO3+H2SO4 / 20 °C 3: alkali With sulfuric acid, nitric acid Jordan; Thorpe; Journal of the Chemical Society; vol. 107; (1915); p. 401 View in Reaxys

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F N F

F F

Rx-ID: 33798475 View in Reaxys 138/140 Yield

F N F

F F

Rx-ID: 33798478 View in Reaxys 139/140 Yield

O O

N O

Rx-ID: 4118079 View in Reaxys 140/140 Yield

Conditions & References With N-butylamine in acetic acid, toluene Hohenlohe-Oehringen,K.; Call,L.; Monatshefte fuer Chemie; vol. 99; nb. 4; (1968); p. 1313 - 1319

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View in Reaxys

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