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29 reactions in Reaxys
2018-06-21 21h:22m:20s (UTC)
O
O
1. Query
Search as: Product, As drawn, No mixtures ))
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O
(v5) (v5) (v3) O C– 2+– (v4)(v3) (v3) (v5)CaC – (v4)(v3) O (v9) (v5) –O O O (v3) (v3) (v3) O Ca 2+ – (v6)(v3) O 2+O(v3) (v5) O2+ (v9) OCa Ca (v3) – O O––O C (v3) (v3) (v4) (v3) (v5) (v4)C (v5) (v5)(v5)
O
O
O
Cl
O O
Rx-ID: 39962042 View in Reaxys 1/29 Yield 38 %, 78 %
Conditions & References in tetrahydrofuran, Time= 0.5h, T= -78 - 20 °C , Schlenk technique, Inert atmosphere, Overall yield = 68 percent Wei, Baosheng; Li, Heng; Zhang, Wen-Xiong; Xi, Zhenfeng; Organometallics; vol. 34; nb. 7; (2015); p. 1339 - 1344 View in Reaxys OH
O
O
O
Cl
Rx-ID: 37121270 View in Reaxys 2/29 Yield 87 %
Conditions & References With triethylamine in dichloromethane, T= 0 - 20 °C Correa, Arkaitz; Leon, Thierry; Martin, Ruben; Journal of the American Chemical Society; vol. 136; nb. 3; (2014); p. 1062 1069 View in Reaxys OH
O
O
OH
O
Rx-ID: 30123562 View in Reaxys 3/29 Yield 73 %
Conditions & References With ethyl triphenylphosphonium tribromide, Time= 0.75h, Reflux Jamir, Latonglila; Alimenla; Kumar, Anil; Sinha, Dipak; Sinha, Upasana B.; Synthetic Communications; vol. 41; nb. 1; (2011); p. 147 - 155 View in Reaxys I O O
O I
O
O
O
O O
Rx-ID: 31272873 View in Reaxys 4/29 Yield 61 %, 9 %
Conditions & References Typical procedure for preparation of -(acetoxy)ethylbenzene with ethylbenzene, DIB, I2, and p-toluenesulfonamide: General procedure: (Diacetoxyiodo)benzene (5 mmol, 1.61 g), I2 (0.4 mmol, 102 mg), p-toluenesulfonamide (0.4 mmol, 68.4 mg), and ethylbenzene (2 mmol, 184 mg) were added to dichloroethane (3 mL). The mixture was warmed at 60 °C for 2 h under an argon atmosphere. Then, the mixture was poured into saturated aqueous sodium sulfite solution and extracted with diethyl ether (3 .x. 20 mL). The organic layer was dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the residue was subjected to preparative TLC on silica gel using a mixture of hexane and ethyl acetate (5:1) as an eluent to give α(acetoxy)ethylbenzene in 63percent yield.
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With iodine, toluene-4-sulfonamide in 1,2-dichloro-ethane, Time= 2h, T= 60 °C , Inert atmosphere Baba, Haruka; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron Letters; vol. 52; nb. 33; (2011); p. 4303 - 4307 View in Reaxys O
O
O
O
O
Rx-ID: 33473934 View in Reaxys 5/29 Yield 98 %
Conditions & References With [Zn(BH4)2(nmi)] in tetrahydrofuran, Time= 8h, Reflux Setamdideh, Davood; Khezri, Behrooz; Asian Journal of Chemistry; vol. 22; nb. 7; (2010); p. 5766 - 5772 View in Reaxys O O
O
OH
O
Rx-ID: 9599152 View in Reaxys 6/29 Yield
Conditions & References With sodium nitrate, H5PV2Mo10O40, Time= 14h, T= 80 °C Khenkin, Alexander M.; Neumann, Ronny; Journal of the American Chemical Society; vol. 126; nb. 20; (2004); p. 6356 6362 View in Reaxys OH
O
O
O
O
O
Rx-ID: 557921 View in Reaxys 7/29 Yield 77 %
Conditions & References Time= 3h, Heating Strazzolini, Paolo; Giumanini, Angelo G.; Verardo, Giancarlo; Tetrahedron; vol. 50; nb. 1; (1994); p. 217 - 254 View in Reaxys T= 100 °C Barbier; Chemische Berichte; vol. 8; (1875); p. 829; Annales de Chimie (Cachan, France); vol. <5> 7; (1876); p. 507 View in Reaxys With pyridine Kuhn; Wassermann; Chemische Berichte; vol. 58; (1925); p. 2230 View in Reaxys Hattori, Kazuyuki; Sajiki, Hironao; Hirota, Kosaku; Tetrahedron; vol. 57; nb. 23; (2001); p. 4817 - 4824 View in Reaxys in pyridine Ohashi, Mamoru; Furukawa, Yuji; Tsujimoto, Kazuo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1980); p. 2613 - 2616 View in Reaxys
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De Voss, James J.; Sibbesen, Ole; Zhang, Zhoupeng; Ortiz De Montellano, Paul R.; Journal of the American Chemical Society; vol. 119; nb. 24; (1997); p. 5489 - 5498 View in Reaxys Cl
OH
O
O
Rx-ID: 1991125 View in Reaxys 8/29 Yield
Conditions & References
84 %
With acetyl chloride in dichloromethane, 1.) 0 deg C, 2.) room temperature, 1 h, Yields of byproduct given Strazzolini, Paolo; Giumanini, Angelo G.; Verardo, Giancarlo; Tetrahedron; vol. 50; nb. 1; (1994); p. 217 - 254 View in Reaxys Cl
OH
O
O
O
Cl
Rx-ID: 3316367 View in Reaxys 9/29 Yield
Conditions & References
83 %
in dichloromethane, 1.) 0 deg C, 2.) room temperature, 1 h, Yield given Strazzolini, Paolo; Giumanini, Angelo G.; Verardo, Giancarlo; Tetrahedron; vol. 50; nb. 1; (1994); p. 217 - 254 View in Reaxys
O
OH
O
O
O
O
P
O
Rx-ID: 1834302 View in Reaxys 10/29 Yield
Conditions & References
0.25 g, 0.8 g, 0.85 g
With acetic acid, phosphorous acid trimethyl ester, Time= 24h, Ambient temperature, var. temp. and time, Mechanism Fuzhenkova, A. V.; Tyryshkin, N. I.; Russian Journal of General Chemistry; vol. 63; nb. 1.1; (1993); p. 76 - 80; Zhurnal Obshchei Khimii; vol. 63; nb. 1; (1993); p. 106 - 110 View in Reaxys
0.25 g, 0.8 g, 0.85 g
With acetic acid, phosphorous acid trimethyl ester, Time= 24h, Ambient temperature Fuzhenkova, A. V.; Tyryshkin, N. I.; Russian Journal of General Chemistry; vol. 63; nb. 1.1; (1993); p. 76 - 80; Zhurnal Obshchei Khimii; vol. 63; nb. 1; (1993); p. 106 - 110 View in Reaxys
O
O
O
O
OH
O
O
P
O
Rx-ID: 2880002 View in Reaxys 11/29
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Yield
Conditions & References
0.7 g, 0.75 g With phosphorous acid trimethyl ester, Time= 0.333333h, T= 20 °C Fuzhenkova, A. V.; Tyryshkin, N. I.; Russian Journal of General Chemistry; vol. 63; nb. 1.1; (1993); p. 76 - 80; Zhurnal Obshchei Khimii; vol. 63; nb. 1; (1993); p. 106 - 110 View in Reaxys
O
O
O
O
O O
P
O
P
O
O
Rx-ID: 3873247 View in Reaxys 12/29 Yield
Conditions & References
0.7 g, 0.75 g With acetic acid, Time= 0.333333h, T= 20 °C Fuzhenkova, A. V.; Tyryshkin, N. I.; Russian Journal of General Chemistry; vol. 63; nb. 1.1; (1993); p. 76 - 80; Zhurnal Obshchei Khimii; vol. 63; nb. 1; (1993); p. 106 - 110 View in Reaxys
O
O O
Rx-ID: 2106558 View in Reaxys 13/29 Yield 98 % Chromat.
Conditions & References With iron(III) chloride in acetonitrile, Time= 1h, T= 80 °C Tyryshkin, N. I.; Vedernikov, A. N.; Solomonov, B. N.; Garifzyanova, G. G.; J. Gen. Chem. USSR (Engl. Transl.); vol. 62; nb. 2.2; (1992); p. 375 - 378,303 - 305 View in Reaxys O
O
OH
O
Rx-ID: 2879864 View in Reaxys 14/29 Yield 12 %
Conditions & References With manganese triacetate, acetylacetone, Time= 0.05h, Heating Nishino, Hiroshi; Kamachi, Hironori; Baba, Harumi; Kurosawa, Kazu; Journal of Organic Chemistry; vol. 57; nb. 13; (1992); p. 3551 - 3557 View in Reaxys With cobalt(III) acetate, Time= 2h, T= 60 °C , other temperature, Mechanism, Product distribution Baciocchi, Enrico; Rol, Cesare; Sebastiani, Giovanni V.; Gazzetta Chimica Italiana; vol. 112; nb. 11/12; (1982); p. 513 - 518 View in Reaxys With cobalt(III) acetate, Time= 2h Baciocchi, Enrico; Rol, Cesare; Sebastiani, Giovanni V.; Gazzetta Chimica Italiana; vol. 112; nb. 11/12; (1982); p. 513 - 518 View in Reaxys
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5/10
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O
OH O
(v2)
(v2)–
O–
O
O
O
Mn3+ (v3)
O–
(v2)
O
O
O
Rx-ID: 3951277 View in Reaxys 15/29 Yield
Conditions & References
55 %, 23 %
With <Mn3O(OAc)6(OAc)(HOAc)>*5H2O, lithium chloride in acetic acid, Time= 2h, Heating Futami; Hishino; Kurosawa; Bulletin of the Chemical Society of Japan; vol. 62; nb. 11; (1989); p. 3567 - 3571 View in Reaxys Br –O
O
Br
O
O
Na +
Rx-ID: 1767501 View in Reaxys 16/29 Yield
Conditions & References
8 %, 48 %
With dipotassium peroxodisulfate, lithium bromide in acetic acid, Time= 6h, T= 113 °C Citterio, Attilio; Santi, Roberto; Pagani, Anselmo; Journal of Organic Chemistry; vol. 52; nb. 22; (1987); p. 4925 - 4927 View in Reaxys O O
O
O
O O
O
O
O
O
O
O O
Rx-ID: 2345445 View in Reaxys 17/29 Yield
Conditions & References With lithium in tetrahydrofuran, other reagents, other solvent, Mechanism, Product distribution Honzl, Jan; Lovy, Jan; Tetrahedron; vol. 40; nb. 10; (1984); p. 1885 - 1892 View in Reaxys 2H
O
2H
2
2
H
O
H O
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.
H
2H
H
2
2
Na +
O–
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2H 2H
2H
O
2H
O
O
O
2H
2H
O
Rx-ID: 1767464 View in Reaxys 18/29 Yield
Conditions & References
6.0 % Chromat., 0.5 % Chromat., 5.9 % Chromat.
Ambient temperature, electrolyses in undivided cell, Pt electrodes, c.p.e. at 1.7 V, further conditions, Product distribution, Mechanism Eberson, Lennart; Webber, Andrew; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 36; nb. 1; (1982); p. 53 - 58 View in Reaxys 2H
2H
O
2H
2H
O 2H 2H
2
H
O
2H
O
O
O
2H
2H
O
Rx-ID: 1767465 View in Reaxys 19/29 Yield
Conditions & References
4.8 % Chromat., 0.9 % Chromat., 2.9 % Chromat.
With tetrabutylammonium tetrafluoroborate, Ambient temperature, electrolyses in undivided cell, Pt electrodes, c.c.e. at 0.5 mA cm-2, Product distribution, Mechanism Eberson, Lennart; Webber, Andrew; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 36; nb. 1; (1982); p. 53 - 58 View in Reaxys O
O
OH
O
O O
Rx-ID: 2879865 View in Reaxys 20/29 Yield
Conditions & References
25 % Chromat., 75 % Chromat.
With ammonium cerium(IV) nitrate, Time= 2h, T= 40 °C , Mechanism, Product distribution Baciocchi, Enrico; Rol, Cesare; Sebastiani, Giovanni V.; Gazzetta Chimica Italiana; vol. 112; nb. 11/12; (1982); p. 513 - 518 View in Reaxys O–
O
O
O
2
Li+
C–
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O O O
O
O
O
O
O
O
O O
Rx-ID: 2352248 View in Reaxys 21/29 Yield
Conditions & References
11 %, 5 %, 18 %, 8 %
in tetrahydrofuran, Time= 0.5h Honzl, J.; Metalova, M.; Journal of Organometallic Chemistry; vol. 185; nb. 3; (1980); p. 297 - 306 View in Reaxys O
O
Rx-ID: 7197220 View in Reaxys 22/29 Yield
Conditions & References 2,3-Dimethyl-fluoranthen, Na2Cr2O7, HOAc Praefcke; Weichsel; Tetrahedron Letters; (1976); p. 1787 View in Reaxys Fluoren, Bleitetraacetat Narasimhan; Venkatasubramanian; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 17; (1979); p. 143 View in Reaxys N O
N
–O
O
O
Cr 3+
3
Rx-ID: 4333342 View in Reaxys 23/29 Yield
Conditions & References in water, N,N-dimethyl-formamide Shirafuji,T. et al.; Bulletin of the Chemical Society of Japan; vol. 46; (1973); p. 2249 - 2251 View in Reaxys NH 2
O
N
O
O
O
OH
Rx-ID: 912766 View in Reaxys 24/29 Yield
Conditions & References in acetic acid Horner,L.; Fernekess,H.; Chemische Berichte; vol. 94; (1961); p. 712 - 724
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View in Reaxys O 2H
OH
O
O
O
O
2H
Rx-ID: 559419 View in Reaxys 25/29 Yield
Conditions & References Bunton et al.; Journal of the Chemical Society; (1958); p. 3718 View in Reaxys O O
O
2H
Rx-ID: 22076376 View in Reaxys 26/29 Yield
Conditions & References Reaction Steps: 2 1: LiAlD4 With lithium aluminium deuteride Bunton et al.; Journal of the Chemical Society; (1958); p. 3718 View in Reaxys O O
OH
zinc dust
O
O
HO
O
OH
O
Rx-ID: 7047774 View in Reaxys 27/29 Yield
Conditions & References Kliegl; Chemische Berichte; vol. 62; (1929); p. 1330; Chemische Berichte; vol. 64; (1931); p. 2422 View in Reaxys N O
N O
OH
O
Rx-ID: 643098 View in Reaxys 28/29
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Yield
Conditions & References Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1959 View in Reaxys Staudinger; Gaule; Chemische Berichte; vol. 49; (1916); p. 1959 View in Reaxys O O
HO
OH
O
O
O
O
Rx-ID: 555529 View in Reaxys 29/29 Yield
Conditions & References Schmidt; Mezger; Chemische Berichte; vol. 39; (1906); p. 3899,4928 View in Reaxys Schmidt; Stuetzel; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 4 Anm. 8 View in Reaxys isomere Verbindung vom Schmelzpunkt 208-209grad Schmidt; Mezger; Chemische Berichte; vol. 39; (1906); p. 3899,4928 View in Reaxys Schmidt; Stuetzel; Justus Liebigs Annalen der Chemie; vol. 370; (1909); p. 4 Anm. 8 View in Reaxys
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