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71 reactions in Reaxys
2018-06-01 01h:37m:20s (UTC)
O
1. Query
Search as: Product, As drawn, No mixtures ) AND (RX.PXRN=2045903)) OR ((IDE.XRN=3270345) AND (RX.PXRN=3270345)) OR ((IDE.XRN=3305864) AND (RX.PXRN=3305864)))
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1/25
2018-06-01 01:38:23
O O
Br
O S O
O
Rx-ID: 47898075 View in Reaxys 1/71 Yield
Conditions & References With samarium diiodide in tetrahydrofuran, T= 23 °C , Inert atmosphere Aretz, Christopher D.; Escobedo, Humberto; Cowen, Bryan J.; European Journal of Organic Chemistry; vol. 2018; nb. 16; (2018); p. 1880 - 1884 View in Reaxys
O
O
O
Rx-ID: 47898130 View in Reaxys 2/71 Yield
Conditions & References Reaction Steps: 4 1.1: magnesium; iodine / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 1.2: -15 - 20 °C / Inert atmosphere 2.1: phenyltrimethylammonium tribromide / tetrahydrofuran / 23 °C / Inert atmosphere 3.1: trimethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: samarium diiodide / tetrahydrofuran / 23 °C / Inert atmosphere With samarium diiodide, iodine, phenyltrimethylammonium tribromide, magnesium, trimethylamine in tetrahydrofuran, dichloromethane Aretz, Christopher D.; Escobedo, Humberto; Cowen, Bryan J.; European Journal of Organic Chemistry; vol. 2018; nb. 16; (2018); p. 1880 - 1884 View in Reaxys
O Br
O
O
S O
O
Rx-ID: 47898162 View in Reaxys 3/71 Yield
Conditions & References With samarium diiodide in tetrahydrofuran, T= 23 °C , Inert atmosphere Aretz, Christopher D.; Escobedo, Humberto; Cowen, Bryan J.; European Journal of Organic Chemistry; vol. 2018; nb. 16; (2018); p. 1880 - 1884 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/25
2018-06-01 01:38:23
O HO
O
Rx-ID: 47898178 View in Reaxys 4/71 Yield
Conditions & References Reaction Steps: 3 1: phenyltrimethylammonium tribromide / tetrahydrofuran / 23 °C / Inert atmosphere 2: trimethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3: samarium diiodide / tetrahydrofuran / 23 °C / Inert atmosphere With samarium diiodide, phenyltrimethylammonium tribromide, trimethylamine in tetrahydrofuran, dichloromethane Aretz, Christopher D.; Escobedo, Humberto; Cowen, Bryan J.; European Journal of Organic Chemistry; vol. 2018; nb. 16; (2018); p. 1880 - 1884 View in Reaxys
O
Br
Rx-ID: 47898317 View in Reaxys 5/71 Yield
Conditions & References Reaction Steps: 4 1.1: magnesium; iodine / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 1.2: -15 - 20 °C / Inert atmosphere 2.1: phenyltrimethylammonium tribromide / tetrahydrofuran / 23 °C / Inert atmosphere 3.1: trimethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 4.1: samarium diiodide / tetrahydrofuran / 23 °C / Inert atmosphere With samarium diiodide, iodine, phenyltrimethylammonium tribromide, magnesium, trimethylamine in tetrahydrofuran, dichloromethane Aretz, Christopher D.; Escobedo, Humberto; Cowen, Bryan J.; European Journal of Organic Chemistry; vol. 2018; nb. 16; (2018); p. 1880 - 1884 View in Reaxys
O Br
OH
O
Rx-ID: 47898405 View in Reaxys 6/71 Yield
Conditions & References Reaction Steps: 2 1: trimethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 2: samarium diiodide / tetrahydrofuran / 23 °C / Inert atmosphere With samarium diiodide, trimethylamine in tetrahydrofuran, dichloromethane Aretz, Christopher D.; Escobedo, Humberto; Cowen, Bryan J.; European Journal of Organic Chemistry; vol. 2018; nb. 16; (2018); p. 1880 - 1884 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/25
2018-06-01 01:38:23
O I
HO
O O
O
B
Mo (v12)
O
O
HO
O
Rx-ID: 45748599 View in Reaxys 7/71 Yield
Conditions & References Stage 1: With tetrakis(triphenylphosphine) palladium(0), potassium carbonate in water, benzene, Time= 24h, T= 20 °C , Inert atmosphere, Irradiation, Suzuki-Miyaura Coupling Stage 2: With 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, T= 70 °C , Inert atmosphere, Suzuki-Miyaura Coupling Roslin, Sara; Odell, Luke R.; Chemical Communications; vol. 53; nb. 51; (2017); p. 6895 - 6898 View in Reaxys
O O
Rx-ID: 47065626 View in Reaxys 8/71 Yield
Conditions & References With sodium hydride in diethyl ether, Time= 1h, T= 25 °C Shipilovskikh, Sergei A.; Rubtsov, Aleksandr E.; Malkov, Andrei V.; Organic Letters; vol. 19; nb. 24; (2017); p. 6760 - 6762 View in Reaxys
HO
O O
Rx-ID: 15257667 View in Reaxys 9/71 Yield
Conditions & References Reaction Steps: 2 1: SOCl2; pyridine / benzene / 2 h / 50 °C 2: 9.8 g / AlCl3 / 1 h / Heating With pyridine, aluminium trichloride, thionyl chloride in benzene, 2: Friedel-Crafts acylation Ho, Bin; Michael Crider; Stables, James P; European Journal of Medicinal Chemistry; vol. 36; nb. 3; (2001); p. 265 - 286 View in Reaxys Reaction Steps: 2 1: 4-methyl-morpholine / toluene / 1 h / 25 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium phosphate / toluene / 0.5 h / 110 °C / Inert atmosphere With 4-methyl-morpholine, bis-triphenylphosphine-palladium(II) chloride, potassium phosphate in toluene, 2: |Suzuki Coupling Wu, Hongxiang; Xu, Baiping; Li, Yue; Hong, Fengying; Zhu, Dezhao; Jian, Junsheng; Pu, Xiaoer; Zeng, Zhuo; Journal of Organic Chemistry; vol. 81; nb. 7; (2016); p. 2987 - 2992 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/25
2018-06-01 01:38:23
H
O
O
Rx-ID: 41298149 View in Reaxys 10/71 Yield
Conditions & References With di-tert-butyl peroxide, Time= 1h, T= 180 °C , Microwave irradiation, Inert atmosphere, Sealed tube Zhang, Xinying; Wang, Zhangxin; Fan, Xuesen; Wang, Jianji; Journal of Organic Chemistry; vol. 80; nb. 21; (2015); p. 10660 - 10667 View in Reaxys 9 :Benzaldehyde (1a, 0.5mmol, 53mg) under nitrogen in a pressure tube 35mL, cyclopentane (2b, 10mL) and di-tbutyl peroxide (TBP, 2mmol, 380uL), and then the pressure the tube was sealed and placed in a microwave reaction apparatus, under microwave irradiation at 180 ° C for 1 hour. After completion of the reaction, recovered by distillation of unreacted 2b, the residue was mixed with silica gel by column (petroleum ether / ethyl acetate = 100/1) to give product 3b (48.7mg, 56percent). With di-tert-butyl peroxide, Time= 1h, T= 180 °C , Inert atmosphere, Microwave irradiation, Sealed tube Patent; HENAN NORMAL UNIVERSITY; ZHANG, XINYING; WANG, ZHANGXIN; FAN, XUESEN; GUO, SHENGHAI; (8 pag.); CN105152830; (2016); (B) Chinese View in Reaxys
O HO
O
N
O
N B
O
N
O
HO
Rx-ID: 42387443 View in Reaxys 11/71 Yield
Conditions & References With bis-triphenylphosphine-palladium(II) chloride, potassium phosphate in toluene, Time= 0.5h, T= 110 °C , Inert atmosphere, Suzuki Coupling Wu, Hongxiang; Xu, Baiping; Li, Yue; Hong, Fengying; Zhu, Dezhao; Jian, Junsheng; Pu, Xiaoer; Zeng, Zhuo; Journal of Organic Chemistry; vol. 81; nb. 7; (2016); p. 2987 - 2992 View in Reaxys
O
(v6)
O
O
SH N O
O
S
cyclopentylzinc halide
O
Rx-ID: 42744882 View in Reaxys 12/71 Yield
Conditions & References With bis(1,5-cyclooctadiene)nickel (0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene in tetrahydrofuran, Time= 24h, T= 23 °C Simmons, Bryan J.; Weires, Nicholas A.; Dander, Jacob E.; Garg, Neil K.; ACS Catalysis; vol. 6; nb. 5; (2016); p. 3176 3179 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/25
2018-06-01 01:38:23
O
O HO
N S
O
O
B HO
O
Rx-ID: 44121126 View in Reaxys 13/71 Yield
Conditions & References With bis-triphenylphosphine-palladium(II) chloride, potassium phosphate in toluene, Time= 4h, T= 65 °C , Inert atmosphere, Suzuki Coupling Wu, Hongxiang; Li, Yue; Cui, Ming; Jian, Junsheng; Zeng, Zhuo; Advanced Synthesis and Catalysis; vol. 358; nb. 23; (2016); p. 3876 - 3880 View in Reaxys
N
HO
O
O
B
O HO
Rx-ID: 41237251 View in Reaxys 14/71 Yield
Conditions & References With trifluorormethanesulfonic acid, water, palladium diacetate, 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine in 1,2-dimethoxyethane, Time= 12h, T= 60 °C Yousuf, Md; Das, Tuluma; Adhikari, Susanta; New Journal of Chemistry; vol. 39; nb. 11; (2015); p. 8763 - 8770 View in Reaxys
OH O O
HO
Rx-ID: 37261133 View in Reaxys 15/71 Yield
Conditions & References With oxygen, copper diacetate in dimethyl sulfoxide, Time= 10h, T= 120 °C , Sealed tube Feng, Qiang; Song, Qiuling; Journal of Organic Chemistry; vol. 79; nb. 4; (2014); p. 1867 - 1871 View in Reaxys
Br Mg
Br
O
O
O
Rx-ID: 38749086 View in Reaxys 16/71 Yield
Conditions & References Stage 1: With iodine, lithium chloride in tetrahydrofuran, diethyl ether, Inert atmosphere, Cooling with ice Stage 2: in tetrahydrofuran, diethyl ether, Time= 0.0166667h, T= 20 °C , p= 5171.62Torr , Flow reactor Stage 3:Further stages
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
6/25
2018-06-01 01:38:23
Wu, Jie; Yang, Xiaoqing; He, Zhi; Mao, Xianwen; Hatton, T. Alan; Jamison, Timothy F.; Angewandte Chemie - International Edition; vol. 53; nb. 32; (2014); p. 8416 - 8420; Angew. Chem.; vol. 126; nb. 32; (2014); p. 8556 - 8560,5 View in Reaxys
OH O
F O
O F
B–
K+
F
Rx-ID: 30786420 View in Reaxys 17/71 Yield
Conditions & References With dipotassium peroxodisulfate, palladium diacetate in water, dimethyl sulfoxide, Time= 3h, T= 20 °C Li, Mingzong; Wang, Cong; Ge, Haibo; Organic Letters; vol. 13; nb. 8; (2011); p. 2062 - 2064 View in Reaxys
O
HO
O
Br
Rx-ID: 26019865 View in Reaxys 18/71 Yield
Conditions & References
84 %
With diethylzinc in dichloromethane, Time= 2h, T= 20 °C Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 - 3522 View in Reaxys
Br O
HO
Rx-ID: 26019918 View in Reaxys 19/71 Yield
Conditions & References With diethylzinc in dichloromethane, Time= 2h, T= 20 °C Li, Lezhen; Cai, Peijie; Guo, Qingxiang; Xue, Song; Journal of Organic Chemistry; vol. 73; nb. 9; (2008); p. 3516 - 3522 View in Reaxys
O
O
2H
Rx-ID: 307812 View in Reaxys 20/71 Yield
Conditions & References With water-d2
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7/25
2018-06-01 01:38:23
Emmons; Hawthorne; Journal of the American Chemical Society; vol. 78; (1956); p. 5593,5594 View in Reaxys Stage 1: With potassium hexamethylsilazane in toluene, Time= 3.5h, T= 20 °C Stage 2: With methyl alcohol-d in toluene, Time= 0.166667h, cooling Masumoto, Shuji; Suzuki, Masato; Kanai, Motomu; Shibasaki, Masakatsu; Tetrahedron; vol. 60; nb. 46 SPEC. ISS.; (2004); p. 10497 - 10504 View in Reaxys Stage 1: With isourea dilithium salt in tetrahydrofuran, hexane, T= -78 °C Stage 2: With water-d2 in tetrahydrofuran, hexane Coumbarides, Gregory S.; Eames, Jason; Suggate, Michael J.; Weerasooriya, Neluka; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 49; nb. 7; (2006); p. 641 - 652 View in Reaxys Reaction Steps: 2 1.1: LDA / tetrahydrofuran / 0.33 h / -78 °C 1.2: 50 percent / tetrahydrofuran / 3 h / -78 °C 2.1: MeLi / diethyl ether / 20 °C 2.2: tBuOD / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C With methyllithium, lithium diisopropyl amide in tetrahydrofuran, diethyl ether Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys Reaction Steps: 2 1.1: 58 percent / p-TsOH / 12 h / 110 °C 2.1: diethyl ether / 1 h / 20 °C 2.2: CD3COOD / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C With toluene-4-sulfonic acid in diethyl ether Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys
Cl Mg
O
N
Rx-ID: 10529161 View in Reaxys 21/71 Yield
Conditions & References Stage 1: With titanium(IV) isopropylate in diethyl ether, Time= 0.216667h, T= -78 - -50 °C Stage 2: in diethyl ether, Time= 0.5h, T= -50 - -30 °C Stage 3: With hydrogenchloride in diethyl ether, Time= 2h, T= 20 °C Cadoret, Frederic; Retailleau, Pascal; Six, Yvan; Tetrahedron Letters; vol. 47; nb. 44; (2006); p. 7749 - 7753 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
8/25
2018-06-01 01:38:23
HO
O
Rx-ID: 288747 View in Reaxys 22/71 Yield
Conditions & References With chlorine-triphenylphosphine, dimethyl sulfoxide, triethylamine in dichloromethane, Time= 3.25h, T= -78 - 20 °C Bisai, Alakesh; Chandrasekhar; Singh, Vinod K.; Tetrahedron Letters; vol. 43; nb. 46; (2002); p. 8355 - 8357 View in Reaxys With chromium(VI) oxide Mitchovitch; Stojiljkovic; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 236; (1953); p. 2080 View in Reaxys Nightingale; Maienthal; Journal of the American Chemical Society; vol. 72; (1950); p. 4823 View in Reaxys With potassium dichromate Braude; Forbes; Journal of the Chemical Society; (1951); p. 1755,1760 View in Reaxys With phosphotungstate catalyst, dihydrogen peroxide, 1-butyl-3-methylimidazolium Tetrafluoroborate, Time= 4h, Heating Chhikara, Bhupender S.; Chandra, Ramesh; Tandon, Vibha; Journal of Catalysis; vol. 230; nb. 2; (2005); p. 436 - 439 View in Reaxys
HO
O
Rx-ID: 9951859 View in Reaxys 23/71 Yield
Conditions & References With Cp*RuCl(Ph2P(CH2)2NH2-κ2-P,N), potassium tert-butylate in toluene, Time= 1h, T= 30 °C Ito, Masato; Kitahara, Sachiko; Ikariya, Takao; Journal of the American Chemical Society; vol. 127; nb. 17; (2005); p. 6172 - 6173 View in Reaxys
O S O
O
NH N
Rx-ID: 12960397 View in Reaxys 24/71 Yield
Conditions & References Reaction Steps: 2 1.1: MeLi / diethyl ether / 1.5 h / 20 °C
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
9/25
2018-06-01 01:38:23
1.2: 57 percent / diethyl ether / -78 - 20 °C 2.1: 99 percent Spectr. / Cp*RuCl[Ph2P(CH2)2NH2-κ2-P,N]; t-BuOK / toluene / 1 h / 30 °C With Cp*RuCl(Ph2P(CH2)2NH2-κ2-P,N), potassium tert-butylate, methyllithium in diethyl ether, toluene Ito, Masato; Kitahara, Sachiko; Ikariya, Takao; Journal of the American Chemical Society; vol. 127; nb. 17; (2005); p. 6172 - 6173 View in Reaxys
H
O
SASRIN-maleidobenzoic acid resin O
Rx-ID: 12965137 View in Reaxys 25/71 Yield
Conditions & References Reaction Steps: 2 1.1: MeLi / diethyl ether / 1.5 h / 20 °C 1.2: 57 percent / diethyl ether / -78 - 20 °C 2.1: 99 percent Spectr. / Cp*RuCl[Ph2P(CH2)2NH2-κ2-P,N]; t-BuOK / toluene / 1 h / 30 °C With Cp*RuCl(Ph2P(CH2)2NH2-κ2-P,N), potassium tert-butylate, methyllithium in diethyl ether, toluene Ito, Masato; Kitahara, Sachiko; Ikariya, Takao; Journal of the American Chemical Society; vol. 127; nb. 17; (2005); p. 6172 - 6173 View in Reaxys
O
Si
O
Rx-ID: 9555598 View in Reaxys 26/71 Yield
Conditions & References Stage 1: With Schwartz's reagent in tetrahydrofuran, Time= 1h, T= 20 °C Stage 2: With tetrabutylammonium hexanitratocerate(IV) in tetrahydrofuran, N,N-dimethyl-formamide, Time= 12h, T= 20 °C , Further stages. Azemi, Takushi; Kitamura, Mitsuru; Narasaka, Koichi; Tetrahedron; vol. 60; nb. 6; (2004); p. 1339 - 1344 View in Reaxys
HO
O O
Rx-ID: 4144677 View in Reaxys 27/71 Yield
Conditions & References (i) SOCl2, (ii) /BRN= 969212/, AlCl3, Multistep reaction Thompson,H.W. et al.; Journal of Organic Chemistry; vol. 37; nb. 22; (1972); p. 3531 - 3536 View in Reaxys
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10/25
2018-06-01 01:38:23
With trifluoromethylsulfonic anhydride, phosphoric acid, Time= 4h, T= 80 °C Orjales, Aurelio; Mosquera, Ramon; Toledo, Antonio; Pumar, M. Carmen; Garcia, Neftali; Cortizo, Lourdes; Labeaga, Luis; Innerarity, Ana; Journal of Medicinal Chemistry; vol. 46; nb. 25; (2003); p. 5512 - 5532 View in Reaxys
O
O
O
O
2H
Rx-ID: 9311654 View in Reaxys 28/71 Yield
Conditions & References Stage 1: in diethyl ether, Time= 1h, T= 20 °C Stage 2: With tetradeuterioacetic acid in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys With ethylene glycol-d2, methyllithium in tetrahydrofuran, Product distribution, Further Variations: Reagents Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys Stage 1: in diethyl ether, Time= 1h, T= 20 °C Stage 2: With tetradeuterioacetic acid in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C , Further stages. Title compound not separated from byproducts. Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys
O
O
O
Si 2H
Rx-ID: 9343050 View in Reaxys 29/71 Yield
Conditions & References Stage 1: With methyllithium in diethyl ether, T= 20 °C Stage 2: With tert-butyl alcohol-d in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C , Title compound not separated from byproducts Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys Stage 1: With methyllithium in diethyl ether, T= 20 °C Stage 2: With tert-butyl alcohol-d in tetrahydrofuran, diethyl ether, Time= 0.5h, T= -78 °C , Further stages. Title compound not separated from byproducts. Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
11/25
2018-06-01 01:38:23
View in Reaxys
Cl
O O
Br–
+Mg
Rx-ID: 9383511 View in Reaxys 30/71 Yield
Conditions & References With vanadium(III) chloride in diethyl ether, dichloromethane, T= -78 - 20 °C Qin, Jun; Friestad, Gregory K.; Tetrahedron; vol. 59; nb. 34; (2003); p. 6393 - 6402 View in Reaxys
O
O
Si 2H
Rx-ID: 14310925 View in Reaxys 31/71 Yield
Conditions & References Reaction Steps: 3 1.1: MeLi / diethyl ether / 20 °C 1.2: tBuOD / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 2.1: 58 percent / p-TsOH / 12 h / 110 °C 3.1: diethyl ether / 1 h / 20 °C 3.2: CD3COOD / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C With methyllithium, toluene-4-sulfonic acid in diethyl ether Eames, Jason; Coumbarides, Gregory S.; Suggate, Michael J.; Weerasooriya, Neluka; European Journal of Organic Chemistry; nb. 4; (2003); p. 634 - 641 View in Reaxys
Cl
O O
Rx-ID: 846839 View in Reaxys 32/71 Yield
Conditions & References With aluminium trichloride Hey; Musgrave; Journal of the Chemical Society; (1949); p. 3156,3160 View in Reaxys With aluminium trichloride, Time= 16h, Ambient temperature Hartmann; Batzl; European Journal of Medicinal Chemistry; vol. 27; nb. 5; (1992); p. 537 - 544 View in Reaxys With aluminium trichloride, Time= 1h, Heating, Friedel-Crafts acylation Ho, Bin; Michael Crider; Stables, James P; European Journal of Medicinal Chemistry; vol. 36; nb. 3; (2001); p. 265 - 286
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
12/25
2018-06-01 01:38:23
View in Reaxys
OH HO
O
O
Rx-ID: 4869729 View in Reaxys 33/71 Yield
Conditions & References
12 %
With potassium superoxide, 2-Nitrobenzenesulfonyl chloride in acetonitrile, Time= 5h, T= -20 °C Kim II, Yong; Kim, Yong Hae; Tetrahedron Letters; vol. 39; nb. 7; (1998); p. 639 - 642 View in Reaxys
Br
O
O
Cl
Rx-ID: 2705316 View in Reaxys 34/71 Yield
Conditions & References With lithium bromide, zinc, 1.) THF, reflux, 2.5 h, 2.) THF, from -45 deg C up to room temperature over 4 h, Yield given. Multistep reaction Hanson, Mark V.; Tetrahedron Letters; vol. 35; nb. 39; (1994); p. 7205 - 7208 View in Reaxys With lithium bromide, zinc, 1.) THF, reflux, 2.5 h, 2.) -45 deg C -> room temperature, 4 h, Yield given. Multistep reaction Rieke, Reuben D.; Hanson, Mark V.; Brown, Jeffrey D.; Niu, Q. Jason; Journal of Organic Chemistry; vol. 61; nb. 8; (1996); p. 2726 - 2730 View in Reaxys
O
Se O Si
Rx-ID: 3710760 View in Reaxys 35/71 Yield
Conditions & References With naphthalene-1,4-dicarbonitrile in water, acetonitrile, Irradiation Pandey, Ganesh; Sochanchingwung, R.; Journal of the Chemical Society, Chemical Communications; nb. 17; (1994); p. 1945 - 1946 View in Reaxys
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13/25
2018-06-01 01:38:23
O Se
O
Rx-ID: 18406524 View in Reaxys 36/71 Yield
Conditions & References Reaction Steps: 2 1: 70 percent / NEt3, NaI / acetonitrile / 0.5 h / Ambient temperature 2: 80 percent / 1,4-dicyanonaphthalene / acetonitrile; H2O / Irradiation With naphthalene-1,4-dicarbonitrile, triethylamine, sodium iodide in water, acetonitrile Pandey, Ganesh; Sochanchingwung, R.; Journal of the Chemical Society, Chemical Communications; nb. 17; (1994); p. 1945 - 1946 View in Reaxys
H
O
O
Rx-ID: 2688809 View in Reaxys 37/71 Yield
Conditions & References With carbon monoxide, dodecacarbonyl-triangulo-triruthenium, Time= 48h, T= 200 °C , p= 14710.2Torr Kondo, Teruyuki; Akazome, Motohiro; Tsuji, Yasushi; Watanabe, Yoshihisa; Journal of Organic Chemistry; vol. 55; nb. 4; (1990); p. 1286 - 1291 View in Reaxys H O
HO
HO
HO
O
O
O
O
Rx-ID: 1586498 View in Reaxys 38/71 Yield
Conditions & References With oxygen, p= 4Torr , Irradiation, effect of gas phase acid-induced ring opening, Product distribution, Mechanism Crotti, P.; Macchia, F.; Pizzabiocca, A.; Renzi, G.; Speranza, M.; Tetrahedron Letters; vol. 28; nb. 29; (1987); p. 3393 - 3396 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
N
Li
S O O
N
O
Rx-ID: 2926157 View in Reaxys 39/71 Yield
Conditions & References in tetrahydrofuran, Ambient temperature Clerici, Francesca; Gelmi, Maria Luisa; Rossi, Luisa Maria; Synthesis; nb. 11; (1987); p. 1025 - 1027 View in Reaxys
O Br
O
Br–
+Mg
O
Rx-ID: 1550174 View in Reaxys 40/71 Yield
Conditions & References Mechanism Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether, r.t., 2 h; 2.) THF, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys
O
O
Rx-ID: 1987942 View in Reaxys 41/71 Yield
Conditions & References With hydrogen Zhang, Pang; Li, Lian-chu; Synthetic Communications; vol. 16; nb. 8; (1986); p. 957 - 966 View in Reaxys
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N O
H 2N
O
Cl
HN
H
HO HO
Rx-ID: 3664648 View in Reaxys 42/71 Yield 17 %
Conditions & References With hydrogenchloride, Time= 1h, Heating Epsztajn, Jan; Bieniek, Adam; Plotka, Mieczyslaw W.; Journal of Chemical Research, Miniprint; nb. 1; (1986); p. 442 - 474 View in Reaxys
O Cl
O
Mg
O
Rx-ID: 3794821 View in Reaxys 43/71 Yield
Conditions & References 1.) ether; 2.) benzene, reflux, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether, r.t., 2 h; 2.) THF, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys
O Cl
Br–
O
+Mg
O
Rx-ID: 3794858 View in Reaxys 44/71 Yield
Conditions & References various educt ratios; study of solvent effect using various solvents, Product distribution, Mechanism Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether; 2.) benzene, reflux, Yield given. Multistep reaction. Yields of byproduct given Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys 1.) ether, r.t., 2 h; 2.) THF, reflux, 12 h, Yield given. Multistep reaction. Yields of byproduct given
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Hori, Mikio; Kataoka, Tadashi; Shimizu, Hiroshi; Imai, Eiji; Iwamura, Tatsunori; Maeda, Kaori; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3599 - 3605 View in Reaxys
O N
O
OH
Rx-ID: 18598029 View in Reaxys 45/71 Yield
Conditions & References Reaction Steps: 3 1: 82 percent / xylene / 30 h / Heating 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then to r.t., 1 h, 2.) -78 deg C, 30 min; 25-30 deg C, 3 h 3: 28 percent / 15percent HCl / 1 h / Heating With hydrogenchloride, n-butyllithium in xylene Epsztajn, Jan; Bieniek, Adam; Plotka, Mieczyslaw W.; Journal of Chemical Research, Miniprint; nb. 1; (1986); p. 442 - 474 View in Reaxys
O N
O
N H
Rx-ID: 18602165 View in Reaxys 46/71 Yield
Conditions & References Reaction Steps: 2 1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then to r.t., 1 h, 2.) -78 deg C, 30 min; 25-30 deg C, 3 h 2: 28 percent / 15percent HCl / 1 h / Heating With hydrogenchloride, n-butyllithium Epsztajn, Jan; Bieniek, Adam; Plotka, Mieczyslaw W.; Journal of Chemical Research, Miniprint; nb. 1; (1986); p. 442 - 474 View in Reaxys
O
N
O
Rx-ID: 19186858 View in Reaxys 47/71 Yield
Conditions & References Reaction Steps: 4 1: Et3N / 0 °C 2: H2 3: 8.7 percent / toluene / 150 - 260 °C / Heating 4: 38.5 percent / H2 With hydrogen, triethylamine in toluene Zhang, Pang; Li, Lian-chu; Synthetic Communications; vol. 16; nb. 8; (1986); p. 957 - 966 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
O
WCl6 Cl
Rx-ID: 19202050 View in Reaxys 48/71 Yield
Conditions & References Reaction Steps: 4 1: Et3N / 0 °C 2: H2 3: 8.7 percent / toluene / 150 - 260 °C / Heating 4: 38.5 percent / H2 With hydrogen, triethylamine in toluene Zhang, Pang; Li, Lian-chu; Synthetic Communications; vol. 16; nb. 8; (1986); p. 957 - 966 View in Reaxys
O
O N
O
Rx-ID: 19211684 View in Reaxys 49/71 Yield
Conditions & References Reaction Steps: 2 1: 8.7 percent / toluene / 150 - 260 °C / Heating 2: 38.5 percent / H2 With hydrogen in toluene Zhang, Pang; Li, Lian-chu; Synthetic Communications; vol. 16; nb. 8; (1986); p. 957 - 966 View in Reaxys
O
O N
O
Rx-ID: 19211866 View in Reaxys 50/71 Yield
Conditions & References Reaction Steps: 3 1: H2 2: 8.7 percent / toluene / 150 - 260 °C / Heating 3: 38.5 percent / H2 With hydrogen in toluene Zhang, Pang; Li, Lian-chu; Synthetic Communications; vol. 16; nb. 8; (1986); p. 957 - 966 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
18/25
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O Cl
O
Rx-ID: 2105123 View in Reaxys 51/71 Yield
Conditions & References With sodium hydroxide in 1,4-dioxane, water Bird, Roger; Griffiths, Gwerydd; Griffiths, Gwynfor F.; Stirling, Charles J. M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 579 - 584 View in Reaxys Reaction Steps: 2 1: 82 percent / lithium bromide / butan-2-one; 2-methyl-propan-2-ol / 12 h / Heating 2: 91 percent / sodium hydroxide / dioxane; H2O / 36 h / 60 °C With sodium hydroxide, lithium bromide in 1,4-dioxane, water, butanone, tert-butyl alcohol Bird, Roger; Griffiths, Gwerydd; Griffiths, Gwynfor F.; Stirling, Charles J. M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 579 - 584 View in Reaxys
O Br
O
Rx-ID: 2157706 View in Reaxys 52/71 Yield
Conditions & References With sodium hydroxide in 1,4-dioxane, water, Time= 36h, T= 60 °C Bird, Roger; Griffiths, Gwerydd; Griffiths, Gwynfor F.; Stirling, Charles J. M.; Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999); (1982); p. 579 - 584 View in Reaxys
O
Rx-ID: 7250184 View in Reaxys 53/71 Yield
Conditions & References Crouzet,J.; Giral,L.; Bulletin de la Societe Chimique de France; (1968); p. 4842 - 4850 View in Reaxys Salesskaja; Nezezkaja; Journal of Organic Chemistry USSR (English Translation); vol. 5; (1969); p. 1563; Zhurnal Organicheskoi Khimii; vol. 5; (1969); p. 1605 View in Reaxys Chastrette et al.; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 286; (1978); p. 679 View in Reaxys Scanlan; MacKenzie; Journal of Organic Chemistry; vol. 37; (1972); p. 1579,1581 View in Reaxys Axiotis et al.; Journal of Organometallic Chemistry; vol. 166; (1979); p. 87,92, 99
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View in Reaxys Patent; Geigy; FR1406708; (1965); ; vol. 63; nb. 13151b; (1965) View in Reaxys Patent; Knowles, Arthur (DuPont); US3686415; (1972); ; vol. 78; nb. 3808r View in Reaxys Patent; E.J. du Pont de Nemours + Co.; US3764621; (1968); ; vol. 80; nb. 14655 View in Reaxys Patent; Knowles; US3689566; (1968); ; vol. 78; nb. 97198 View in Reaxys Patent; E.I. du Pont de Nemours + Co.; US3683040; (1967); ; vol. 77; nb. 114405 View in Reaxys Patent; E.I. du Pont de Nemours + Co.; US3679805; (1967); ; vol. 77; nb. 113892 View in Reaxys Niyazov; Khabaeva; Izvestiya Akademii Nauk Turkmenskoi SSR, Seriya Fiziko-Tekhnicheskikh, Khimicheskikh i Geologicheskikh Nauk; vol. 1; (1962); p. 103; ; vol. 58; nb. 469 View in Reaxys Bobysheva et al.; Journal of Organic Chemistry USSR (English Translation); vol. 8; (1972); p. 2109; Zhurnal Organicheskoi Khimii; vol. 8; (1972); p. 2062 View in Reaxys Christol et al.; Bulletin de la Societe Chimique de France; (1961); p. 2317 View in Reaxys Botteron; Wood; Journal of Organic Chemistry; vol. 30; (1965); p. 3871,3874 View in Reaxys Patent; Schering AG; DE2702911; (1978); ; vol. 90; nb. 22619 View in Reaxys Patent; E.I. du Pont de Nemours and Co.; US3697594; (1968); ; vol. 78; nb. 15645 View in Reaxys Padwa; Eastman; Journal of the American Chemical Society; vol. 91; (1969); p. 462 View in Reaxys
O
Rx-ID: 1050709 View in Reaxys 54/71 Yield
Conditions & References With methanol, thallium(III) nitrate McKillop,A. et al.; Journal of the American Chemical Society; vol. 95; (1973); p. 3635 - 3640 View in Reaxys
Br Mg
O
N
Rx-ID: 658111 View in Reaxys 55/71 Yield
Conditions & References Crouzet,J. et al.; Bulletin de la Societe Chimique de France; (1967); p. 3722 - 3729 View in Reaxys Tilford; Van Campen; Journal of the American Chemical Society; vol. 76; (1954); p. 2431,2435, 2438; Journal of the American Chemical Society; vol. 79; (1957); p. 6575 View in Reaxys Smith et al.; Journal of the American Chemical Society; vol. 76; (1954); p. 4564,4567
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View in Reaxys
N+ O
I–
HO
Rx-ID: 1376425 View in Reaxys 56/71 Yield
Conditions & References (i) Ag2O, (ii) (heating), Multistep reaction Mandrou,A.-M. et al.; Bulletin de la Societe Chimique de France; (1962); p. 1546 - 1554 View in Reaxys
H 2N
O
O
Rx-ID: 1152085 View in Reaxys 57/71 Yield
Conditions & References With lithium aluminium tetrahydride in diethyl ether, Heating Eistert,B.; Wurzler,H.; Justus Liebigs Annalen der Chemie; vol. 650; (1961); p. 157 - 170 View in Reaxys
O
O O
O
Rx-ID: 1259773 View in Reaxys 58/71 Yield
Conditions & References With tin(IV) chloride Eistert,B.; Justus Liebigs Annalen der Chemie; vol. 650; (1961); p. 133 - 156 View in Reaxys
O N
O
Rx-ID: 22722388 View in Reaxys 59/71 Yield
Conditions & References Reaction Steps: 2 1: diethyl ether / Heating 2: LiAlH4 / diethyl ether / Heating With lithium aluminium tetrahydride in diethyl ether
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Eistert,B.; Wurzler,H.; Justus Liebigs Annalen der Chemie; vol. 650; (1961); p. 157 - 170 View in Reaxys
O 2H
O
2H
2
2H
2
H
H
2H
2H
2H
Rx-ID: 305871 View in Reaxys 60/71 Yield
Conditions & References Emmons; Hawthorne; Journal of the American Chemical Society; vol. 78; (1956); p. 5593,5594 View in Reaxys
H 2N
O
OH
O
O N
OH
HO
Rx-ID: 7987437 View in Reaxys 61/71 Yield
Conditions & References Curtin; Schmukler; Journal of the American Chemical Society; vol. 77; (1955); p. 1105,1108 View in Reaxys
Cl O
Ag2O HO
O
Rx-ID: 7987438 View in Reaxys 62/71 Yield
Conditions & References Curtin; Schmukler; Journal of the American Chemical Society; vol. 77; (1955); p. 1105,1108 View in Reaxys
H 2N
O
OH
O N
OH
HO
O
1-phenyl-cyclohexane-1,2-diolene O
Rx-ID: 7987439 View in Reaxys 63/71 Yield
Conditions & References Curtin; Schmukler; Journal of the American Chemical Society; vol. 77; (1955); p. 1105,1108 View in Reaxys
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O
O
O
Br–
+Mg
Cl
Rx-ID: 461593 View in Reaxys 64/71 Yield
Conditions & References T= 130 °C Cauquil; Rouzaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 237; (1953); p. 1720 View in Reaxys
Cl Mg
O
Rx-ID: 22146195 View in Reaxys 65/71 Yield
Conditions & References Reaction Steps: 2 1: diethyl ether 2: CrO3 With chromium(VI) oxide, diethyl ether Mitchovitch; Stojiljkovic; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 236; (1953); p. 2080 View in Reaxys Nightingale; Maienthal; Journal of the American Chemical Society; vol. 72; (1950); p. 4823 View in Reaxys
H
O
O
Rx-ID: 22146417 View in Reaxys 66/71 Yield
Conditions & References Reaction Steps: 2 1: diethyl ether 2: CrO3 With chromium(VI) oxide, diethyl ether Mitchovitch; Stojiljkovic; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 236; (1953); p. 2080 View in Reaxys Nightingale; Maienthal; Journal of the American Chemical Society; vol. 72; (1950); p. 4823 View in Reaxys Reaction Steps: 2 1: diethyl ether 2: CrO3 With chromium(VI) oxide, diethyl ether Mitchovitch; Stojiljkovic; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 236; (1953); p. 2080
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View in Reaxys Nightingale; Maienthal; Journal of the American Chemical Society; vol. 72; (1950); p. 4823 View in Reaxys
Br Mg
O
Rx-ID: 22154186 View in Reaxys 67/71 Yield
Conditions & References Reaction Steps: 2 1: diethyl ether 2: CrO3 With chromium(VI) oxide, diethyl ether Mitchovitch; Stojiljkovic; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 236; (1953); p. 2080 View in Reaxys Nightingale; Maienthal; Journal of the American Chemical Society; vol. 72; (1950); p. 4823 View in Reaxys
O
N2O O
Rx-ID: 7250185 View in Reaxys 68/71 Yield
Conditions & References T= 300 °C , p= 367754Torr Bridson-Jones; Buckley; Journal of the Chemical Society; (1951); p. 3009,3010,1014 View in Reaxys
O
O
Rx-ID: 39637000 View in Reaxys 69/71 Yield
Conditions & References With Grubb's 2nd generation catalyst, formic acid, sodium formate in tetrahydrofuran, Time= 6h, T= 80 °C , Inert atmosphere Grela, Karol; Zieliski, Grzegorz Krzysztof; Samojlowicz, Cezary; Wdowik, Tomasz; Grela, Karol; View in Reaxys
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O
O
O
O
Rx-ID: 39637041 View in Reaxys 70/71 Yield
Conditions & References Reaction Steps: 3 1: lithium chloride / water; dimethyl sulfoxide / 2 h / 180 °C / Microwave irradiation; Inert atmosphere 2: Grubb's 2nd generation catalyst / dichloromethane / 1 h / 40 °C / Inert atmosphere 3: Grubb's 2nd generation catalyst; formic acid; sodium formate / tetrahydrofuran / 6 h / 80 °C / Inert atmosphere With Grubb's 2nd generation catalyst, formic acid, sodium formate, lithium chloride in tetrahydrofuran, dichloromethane, water, dimethyl sulfoxide Grela, Karol; Zieliski, Grzegorz Krzysztof; Samojlowicz, Cezary; Wdowik, Tomasz; Grela, Karol; View in Reaxys
O
O
Rx-ID: 39637042 View in Reaxys 71/71 Yield
Conditions & References Reaction Steps: 2 1: Grubb's 2nd generation catalyst / dichloromethane / 1 h / 40 °C / Inert atmosphere 2: Grubb's 2nd generation catalyst; formic acid; sodium formate / tetrahydrofuran / 6 h / 80 °C / Inert atmosphere With Grubb's 2nd generation catalyst, formic acid, sodium formate in tetrahydrofuran, dichloromethane Grela, Karol; Zieliski, Grzegorz Krzysztof; Samojlowicz, Cezary; Wdowik, Tomasz; Grela, Karol; View in Reaxys
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