1,1-Diphenylpropan-2-one [1,1-Diphenylacetone]

Page 1

Reaxys

PubChem

eMolecules

Reactions (82)

Yield

Substances (4)

Citations (101)

Conditions

References

1

Synthesize Find similar 11%

Rx-ID: 7161689 Find similar reactions

With copper(l) iodide; bathophenanthroline; caesium carbonate in tert-butyl alcohol

T=110°C; 24 h; Inert atmosphere; Hide Experimental Procedure

CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N. R.S.); UNIVERSITE MONTPELLIER 2, SCIENCES ET TECHNIQUES; ECOLE NATIONALE SUPERIEURE DE CHIME DE MONTPELLIER; Taillefer, Marc; Monnier, Florian; Tlili, Anis; Danoun, Grégory

Patent: US2015/166464 A1, 2015 ; Location in patent: Paragraph 0426-0427 ; Title/Abstract Full Text Show Details

General procedure: Procedure C [0426] After several standard draining and purging cycles of the tubes with a flow of argon or nitrogen, the reactor is charged with 0.01 mmol (19 mg) of CuI, 1.5 mmol of formula (III) compound, 2 mmol (650 mg) of Cs2CO3, 0.1 mmol of bathophenanthroline and 1 mmol of formula (II) compound (II) if it is a solid. If the formula (II) compound is a liquid, it is added to the reaction medium using a syringe under a flow of nitrogen at ambient temperature followed by the addition of 1 ml of anhydrous, degassed de tert-butanol. The reactor is closed under positive pressure of nitrogen or argon. The reaction mixture is left under agitation and heated to 110° C. for 24 hours. After cooling down to ambient temperature, 13 μL of 1,3-dimethoxybenzene (internal standard) then 1 ml of ethyl acetate are added. A sample of the reaction medium is taken and acidified with 10percent aqueous HCl solution, the organic phase is then filtered through celite and the residue washed in ethyl acetate. The organic phases obtained are combined and washed with brine solution, dried over Na2SO4, filtered and concentrated in vacuo. The product obtained is purified by silica gel chromatography and analysed by NMR. [0427] The results obtained are summarised in the Table below: Kirrstetter,R.G.H.

Chemische Berichte, 1979 , vol. 112, p. 2804 - 2810 Full Text View citing articles Show Details

McKillop,A. et al.

Journal of the American Chemical Society, 1973 , vol. 95, p. 3635 - 3640


Full Text View citing articles Show Details

Auterhoff; Bertram

Archiv der Pharmazie, 1973 , vol. 306, # 12 p. 881 - 888 Title/Abstract Full Text View citing articles Show Details

Kirrmann,A.; Nouri-Bimorghi,R.

Bulletin de la Societe Chimique de France, 1968 , p. 3213 - 3220 Full Text View citing articles Show Details

Buehler,C.A. et al.

Journal of Organic Chemistry, 1961 , vol. 26, p. 1573 - 1577 Full Text View citing articles Show Details

Corey,E.J.; Shulman,J.I.

Journal of Organic Chemistry, 1970 , vol. 35, # 3 p. 777 - 780 Full Text View citing articles Show Details

Mukaiyama et al.

Chemistry Letters, 1977 , p. 179 Full Text Show Details

Cooke; Magnus

Journal of the Chemical Society, Chemical Communications, 1977 , p. 513 Full Text View citing articles Show Details

Fridman et al.

Patent: SU487870 , 1976 ; Ref. Zh., Khim., 1977 , vol. 3, # O67 Full Text Show Details

Wright

Journal of Organic Chemistry, 1960 , vol. 25, p. 1867,1869 Full Text Show Details

Cazes; Julia

Tetrahedron, 1979 , vol. 35, p. 2655,2660 Full Text Show Details

Ito et al.

Tetrahedron Letters, 1979 , p. 2253,2254 Full Text Show Details

Brewster et al.

Journal of Organic Chemistry, 1964 , vol. 29, p. 121,122 Full Text Show Details

Jallabert et al.

Bulletin de la Societe Chimique de France, 1970 , p. 797 Full Text Show Details

Jeffery; Meisters

Journal of Organometallic Chemistry, 1974 , vol. 82, p. 307,311 Full Text Show Details

McKillop et al.

Tetrahedron Letters, 1970 , p. 5275 Full Text View citing articles Show Details

Khaimova et al.

Godishnik na Sofiiskiya Universitet "Sv. Kliment Okhridski", Khimicheski Fakultet, 1960 , vol. 55, p. 67 Chem.Abstr., 1963 , vol. 59, # 9855b Full Text Show Details

Sawaki; Ogata

Journal of the American Chemical Society, 1975 , vol. 97, p. 6983,6984-6989 Full Text Show Details

Golovyashkina; Tsukervanik

Uzb. Khim. Zh., 1962 , vol. 6, p. 56 Chem.Abstr., 1963 , vol. 58, # 3342h Full Text Show Details

Aren et al.

Patent: SU1340032 , 1977 ; Ref. Zh., Khim., 1978 , vol. 14, # O299P Full Text Show Details

Com. Scien. a. Ind. Res. Org.

Patent: US3900505 , 1975 ; Chem.Abstr., vol. 83, # 192881 Full Text Show Details

Tagucki; Takigucki

Yuki Gosei Kagaku Kyokaishi, 1973 , vol. 31, p. 429 Full Text Show Details

Kitamura et al.

Chemistry Letters, 1978 , p. 1223 Full Text Show Details

Hoffmann; Nour

Journal of the Chemical Society, Chemical Communications, 1975 , p. 37 Full Text Show Details

Groebel; Seebach

Chemische Berichte, 1977 , vol. 110, p. 867,871, 874, 876 Full Text Show Details

Posner; Whitten

Tetrahedron Letters, 1970 , p. 4647,4648 Full Text Show Details

Suarez; Orio

Anales de la Asociacion Quimica Argentina (1921-2001), 1977 , vol. 65, p. 163,164, 165, 166, 167 Full Text Show Details

Bagnell et al.

Australian Journal of Chemistry, 1974 , vol. 27, p. 2577,2580 Full Text Show Details

Chaimowa et al.

Doklady Chemistry, 1962 , vol. 143, p. 370


Doklady Akademii Nauk SSSR, 1962 , vol. 143, p. 1374 Full Text Show Details

Benjamin; Collins

Journal of the American Chemical Society, 1961 , vol. 83, p. 3666 Full Text Show Details

Korobicyna et al.

Journal of Organic Chemistry USSR (English Translation), 1969 , vol. 5, p. 1090 Zhurnal Organicheskoi Khimii, 1969 , vol. 5, p. 1109 Full Text Show Details

2

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Rx-ID: 39596753 Find similar reactions

30%

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Stage #1: bis-maleimidodiphenyl-methane acid With n-butyllithium in tetrahydrofuran

T=0°C; 1 h; Inert atmosphere; Stage #2: ethyl acetate in tetrahydrofuran

T=60°C; 16 h; Hide Experimental Procedure

Hendricks, Robert Than; Beigelman, Leonid; Smith, David Bernard; Stoycheva, Antitsa Dimitrova

Patent: US2015/72982 A1, 2015 ; Location in patent: Paragraph 0165; 0166 ; Title/Abstract Full Text Show Details

3:

10166] To a solution of diphenylmethane (250 g, 1.49 mol) in THF (1.5 E) at 0° C. under N2 was added n-l3uEi (549 ml, 1.49 mmol, 2.5 M) dropwise. Afier addition, the reaction was stirred for 1 h at the same temperature. AcOEt (196 g, 2.23 mol) was added dropwise, and then the mixture was kept stirring at 60° C. for 16 h. The reaction was quenched with water, extracted with EtOAc (3x200 mE). The organic phases were washed with brine, dried over anhydrous Na2504, filtered and concentrated. The residue was purified by flash colunm chromatography on silica gel (PE:EA=10: 1) to give A-i as a white solid (100 g, yield: 30percent). ‘H NMR (400 MHz, CDC13): ö 7.41-7.25 (m, 1OH), 5.15 (s, 1H), 2.28 (s, 3H).

3

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92%

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With peracetic acid; 4-acetylamino 2,2,6,6-tetramethylpiperidin-N-oxyl in acetonitrile

T=20°C; 10 h;

A

4

Rx-ID: 40539640 Find similar reactions

Zhang, Shufang; Miao, Chengxia; Xia, Chungu; Sun, Wei

ChemCatChem, 2015 , vol. 7, # 12 p. 1865 - 1870 Title/Abstract Full Text View citing articles Show Details

B

C


Synthesize Find similar Rx-ID: 9457017 Find similar reactions

5

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With 3 A molecular sieve; oxygen; sodium carbonate; Pd((-)-sparteine)2Cl2 in tert-butyl alcohol

T=65°C; 24 h; Title compound not separated from byproducts;

Mandal, Sunil K.; Sigman, Matthew S.

Journal of Organic Chemistry, 2003 , vol. 68, # 19 p. 7535 - 7537 Title/Abstract Full Text View citing articles Show Details

With di-μ-chloro-bis(η4-1,5-cyclooctadiene)diiridium; [bis(triphenyl-λ5-phosphanylidene)ammonium] [Cl]; acetone; potassium hydroxide; N,N'-bis[o-(diphenylphosphino)benzylidene]-(1S,2S)-diaiminocyclohexane in dichloromethane; water; isopropyl alcohol

T=45°C; 32 h; Resolution of racemateInert atmosphere; enantioselective reaction;

Zhang, Juanni; Yang, Xiangren; Zhou, Han; Li, Yanyun; Dong, Zhenrong; Gao, Jingxing

Green Chemistry, 2012 , vol. 14, # 5 p. 1289 - 1292 Title/Abstract Full Text View citing articles Show Details

A

B

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Synthesize Find similar Rx-ID: 34106332 Find similar reactions

6

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Stage #1: With C28H36ClMnN2O2; potassium acetate in dichloromethane; water

0.0833333 h; Stage #2: With N-bromosuccinmide in dichloromethane; water

T=20°C; 2 h; Kinetics; enantioselective reaction;

Xu, Daqian; Wang, Shoufeng; Shen, Zhiqiang; Xia, Chungu; Sun, Wei

Organic and Biomolecular Chemistry, 2012 , vol. 10, # 14 p. 2730 - 2732 Title/Abstract Full Text View citing articles Show Details

A

B

C

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Synthesize Find similar Rx-ID: 29173893


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A: 43% B: 16% C: 28%

7

Stage #1: With bis(η5-cyclopentadienyl)titanium dichloride in tetrahydrofuran

T=20°C; 0.5 h; Inert atmosphere; Stage #2: With sodium dihydrogenphosphate; water in tetrahydrofuran

T=20°C; 0.333333 h; Inert atmosphere;

Rx-ID: 29173912 Find similar reactions

A: 18% B: 28% C: 39%

B

C

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Stage #1: With bis(η5-cyclopentadienyl)titanium dichloride in tetrahydrofuran

T=20°C; 0.5 h; Inert atmosphere; Stage #2: With sodium dihydrogenphosphate; water in tetrahydrofuran

T=20°C; 0.333333 h; Inert atmosphere;

Fernandez-Mateos, Alfonso; Madrazo, Soledad Encinas; Teijon, Pablo Herrero; Gonzalez, Rosa Rubio

European Journal of Organic Chemistry, 2010 , # 5 p. 856 - 861 Title/Abstract Full Text View citing articles Show Details

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102 mg

9

A

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8

Fernandez-Mateos, Alfonso; Madrazo, Soledad Encinas; Teijon, Pablo Herrero; Gonzalez, Rosa Rubio

European Journal of Organic Chemistry, 2010 , # 5 p. 856 - 861 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 10251324 Find similar reactions

With boron trifluoride diethyl etherate in diethyl ether

T=20°C; 0.0166667 h;

Taber, Douglass F.; Tian, Weiwei

Journal of the American Chemical Society, 2006 , vol. 128, # 4 p. 1058 - 1059 Title/Abstract Full Text View citing articles Show Details

A

B

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Synthesize Find similar Rx-ID: 10494146

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Su, Weiping; Raders, Steven; Verkade, John G.; Liao, Xuebin; Hartwig, John F.

Angewandte Chemie - International Edition, 2006 , vol. 45, # 35 p. 5852 - 5855 Title/Abstract Full Text View citing articles Show Details

With manganese(II) fluoride; ZnF2; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethylformamide

T=70°C;

10

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Rx-ID: 12213428 Find similar reactions

Multi-step reaction with 2 steps 1: 0.168 g / mCPBA; NaHCO3 / CH2Cl2 / 0 °C 2: 102 mg / BF3*OEt2 / diethyl ether / 0.02 h / 20 °C View Scheme

Taber, Douglass F.; Tian, Weiwei

Journal of the American Chemical Society, 2006 , vol. 128, # 4 p. 1058 - 1059 Title/Abstract Full Text View citing articles Show Details

11

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Rx-ID: 12244113 Find similar reactions

Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C 1.2: 0.207 g / tetrahydrofuran; hexane / 2 h / 0 °C 2.1: 0.168 g / mCPBA; NaHCO3 / CH2Cl2 / 0 °C 3.1: 102 mg / BF3*OEt2 / diethyl ether / 0.02 h / 20 °C View Scheme

Taber, Douglass F.; Tian, Weiwei

Journal of the American Chemical Society, 2006 , vol. 128, # 4 p. 1058 - 1059 Title/Abstract Full Text View citing articles Show Details

A

B

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12

Synthesize Find similar Rx-ID: 9876142


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A: 9% B: 87%

With gallium(III) chloride; 2-methyl cyclohexane in 1,2-dichloro-ethane

T=80°C; 1 h;

Oshita, Masayuki; Okazaki, Takao; Ohe, Kouichi; Chatani, Naoto

Organic Letters, 2005 , vol. 7, # 2 p. 331 - 334 Title/Abstract Full Text View citing articles Show Details

A

B

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13

Synthesize Find similar Rx-ID: 9950446 Find similar reactions

With [bis(acetoxy)iodo]benzene; potassium bromide; (S,S)-(+)-Jacobsen salene complex in dichloromethane

T=20°C; 1 h; Kinetics; Further Variations:Solvents;

Li, Zhen; Tang, Zhong H.; Hu, Xiao X.; Xia, Chun G.

Chemistry - A European Journal, 2005 , vol. 11, # 4 p. 1210 - 1216 Title/Abstract Full Text View citing articles Show Details

14

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Rx-ID: 13131753 Find similar reactions

Multi-step reaction with 2 steps 1: DIBAL 2: 9 percent / GaCl3; methylcyclohexane / 1,2-dichloro-ethane / 1 h / 80 °C View Scheme

Oshita, Masayuki; Okazaki, Takao; Ohe, Kouichi; Chatani, Naoto

Organic Letters, 2005 , vol. 7, # 2 p. 331 - 334 Title/Abstract Full Text View citing articles Show Details

A

B

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15

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A: 31% B: 24%

With triethylaluminum in hexane; dichloromethane

T=-78 - 0°C; 0.333333 h; Product distribution; Further Variations:Temperatures;

Shionhara, Tomoichi; Suzuki, Keisuke

Synthesis, 2003 , # 1 p. 141 - 146 Title/Abstract Full Text View citing articles Show Details

A

B

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16

Synthesize Find similar Rx-ID: 9391642 Find similar reactions

A: 57% B: 38%

With 3 A molecular sieve; oxygen; (-)-sparteine; Pd((-)-sparteine)2Cl2 in tert-butyl alcohol

T=65°C; 24 h;

Mandal, Sunil K.; Jensen, David R.; Pugsley, Jacob S.; Sigman, Matthew S.

Journal of Organic Chemistry, 2003 , vol. 68, # 11 p. 4600 - 4603 Title/Abstract Full Text View citing articles Show Details

A

B

C

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17

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With zeolite; oxygen in hexane

UV-irradiation;

Clennan, Edward L.; Pan, Gui-Ian

Organic Letters, 2003 , vol. 5, # 26 p. 4979 - 4982 Title/Abstract Full Text View citing articles Show Details

A

B

C

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18

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With zeolite; oxygen in hexane

UV-irradiation;

Clennan, Edward L.; Pan, Gui-Ian

Organic Letters, 2003 , vol. 5, # 26 p. 4979 - 4982 Title/Abstract Full Text View citing articles Show Details

19

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Rx-ID: 9583034 Find similar reactions

With zeolite

T=20°C; 24 h;

Clennan, Edward L.; Pan, Gui-Ian

Organic Letters, 2003 , vol. 5, # 26 p. 4979 - 4982 Title/Abstract Full Text View citing articles Show Details

20

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Rx-ID: 13688387 Find similar reactions

Multi-step reaction with 2 steps 1: O2; zeolite / hexane / UV-irradiation 2: zeolite / 24 h / 20 °C View Scheme

Clennan, Edward L.; Pan, Gui-Ian

Organic Letters, 2003 , vol. 5, # 26 p. 4979 - 4982 Title/Abstract Full Text View citing articles Show Details

21

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65%

With boron trifluoride diethyl etherate in chloroform

T=-40 - 20°C; 168 h;

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Rx-ID: 9039099 Find similar reactions

Sugihara, Yoshiaki; Iimura, Shinya; Nakayama, Juzo

Chemical Communications, 2002 , # 2 p. 134 - 135 Title/Abstract Full Text View citing articles Show Details


A

B

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22

Synthesize Find similar Rx-ID: 5139135 Find similar reactions

With CaY zeolite in hexane

3 h; Ambient temperature; Yield givenYields of byproduct given;

Kao, Hsien-Ming; Grey, Clare P.; Pitchumani, Kasi; Lakshminarasimhan; Ramamurthy

Journal of Physical Chemistry A, 1998 , vol. 102, # 28 p. 5627 - 5638 Title/Abstract Full Text View citing articles Show Details

23

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Rx-ID: 16303127 Find similar reactions

Multi-step reaction with 2 steps 1: p-TsOH / benzene / Heating 2: CaY zeolite / hexane / 3 h / Ambient temperature View Scheme

Kao, Hsien-Ming; Grey, Clare P.; Pitchumani, Kasi; Lakshminarasimhan; Ramamurthy

Journal of Physical Chemistry A, 1998 , vol. 102, # 28 p. 5627 - 5638 Title/Abstract Full Text View citing articles Show Details

24

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69%

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With tetraethylammonium chloride in methanol; dichloromethane

electrolysis;

Rx-ID: 4491738 Find similar reactions

Kimura, Makoto; Kobayashi, Kazutaka; Yamamoto, Yasushi; Sawaki, Yasuhiko

Tetrahedron, 1996 , vol. 52, # 12 p. 4303 - 4310 Title/Abstract Full Text View citing articles Show Details


25

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Rx-ID: 2045739 Find similar reactions

81%

With dinitrogen tetraoxide in acetonitrile

T=-40°C; 0.166667 h;

Shim, Sung Bo; Kim, Kweon; Kim, Yong Hae

Tetrahedron Letters, 1987 , vol. 28, # 6 p. 645 - 648 Title/Abstract Full Text View citing articles Show Details

81%

With dinitrogen tetraoxide in acetonitrile

T=-40°C; 0.166667 h;

Kim, Yong Hae

Phosphorus, Sulfur and Silicon and the Related Elements, 1993 , vol. 74, # 1-4 p. 249 - 260 Title/Abstract Full Text Show Details

26

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Rx-ID: 2095431 Find similar reactions

With 1,4-diaza-bicyclo[2.2.2]octane in xylene

5 h; Heating;

Augelli-Szafran; Blankley; Roth; Trivedi; Bousley; Essenburg; Hamelehle; Krause; Stanfield

Journal of Medicinal Chemistry, 1993 , vol. 36, # 20 p. 2943 - 2949 Title/Abstract Full Text View citing articles Show Details

A

B

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27

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A: 69.8% B: 15.1%

With titanium tetrachloride; zinc in tetrahydrofuran

Heating;

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Shi, Da-Qing; Chen, Jian-Xie; Chai, Wen-Ying; Chen, Wei-Xing; Kao, Tsi-Yu

Tetrahedron Letters, 1993 , vol. 34, # 18 p. 2963 - 2964 Title/Abstract Full Text View citing articles Show Details


A

B

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28

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Rx-ID: 3523154 Find similar reactions

A: 11 % Chromat. B: 88 % Chromat.

With potassium tert-butylate in dimethyl sulfoxide

1 h; Irradiation;

Borosky, Gabriela L.; Pierini, Adriana B.; Rossi, Roberto A.

Journal of Organic Chemistry, 1992 , vol. 57, # 1 p. 247 - 252 Title/Abstract Full Text View citing articles Show Details

A: 11 % Chromat. B: 88 % Chromat.

With potassium tert-butylate in dimethyl sulfoxide

1 h; Irradiation;

Borosky, Gabriela L.; Pierini, Adriana B.; Rossi, Roberto A.

Journal of Organic Chemistry, 1992 , vol. 57, # 1 p. 247 - 252 Title/Abstract Full Text View citing articles Show Details

A

B

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29

Synthesize Find similar Rx-ID: 2046478 Find similar reactions

A: 27% B: 56%

With titanium(III) chloride in tetrahydrofuran; water

T=0°C; 20 h; pH 6.5;

Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki

Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 6 p. 1787 - 1791 Title/Abstract Full Text Show Details

A: 27% B: 56%

With titanium(III) chloride; ammonium acetate in tetrahydrofuran; water

T=0°C; 20 h;

Sera, Akira; Fukumoto, Shoji; Yoneda, Takako; Yamada, Hiroaki

Heterocycles, 1986 , vol. 24, # 3 p. 697 - 702 Title/Abstract Full Text View citing articles Show Details

A

30

B


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A: 84% B: 14%

With titanium(III) chloride in tetrahydrofuran; water

T=35°C; 24 h; pH 6.5;

Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki

Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 6 p. 1787 - 1791 Title/Abstract Full Text Show Details

A: 84% B: 14%

With titanium(III) chloride; ammonium acetate in tetrahydrofuran; water

T=35°C; 24 h;

Sera, Akira; Fukumoto, Shoji; Yoneda, Takako; Yamada, Hiroaki

Heterocycles, 1986 , vol. 24, # 3 p. 697 - 702 Title/Abstract Full Text View citing articles Show Details

A: 84% B: 14%

With titanium(III) chloride in tetrahydrofuran; water

T=35°C; 24 h; pH 6.5;

Sera, Akira; Fukumoto, Shoji; Tamura, Masako; Takabatake, Kiyoshi; Yamada, Hiroaki; Itoh, Kuniaki

Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 6 p. 1787 - 1791 Title/Abstract Full Text Show Details

Hide Details

A: 84% B: 14%

With titanium(III) chloride; ammonium acetate in tetrahydrofuran; water

T=35°C; 24 h;

Sera, Akira; Fukumoto, Shoji; Yoneda, Takako; Yamada, Hiroaki

Heterocycles, 1986 , vol. 24, # 3 p. 697 - 702 Title/Abstract Full Text View citing articles Show Details

31

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Rx-ID: 2351114 Find similar reactions

42%

in tetrahydrofuran; hexane

0.166667 h; Heating;

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Bunce, Richard A.; Dowdy, Eric D.

Synthetic Communications, 1990 , vol. 20, # 19 p. 3007 - 3014 Title/Abstract Full Text Show Details


32

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Rx-ID: 2481354 Find similar reactions

With trifluorormethanesulfonic acid; water

Yield given;

Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi

Journal of Organic Chemistry, 1989 , vol. 54, # 4 p. 733 - 734 Title/Abstract Full Text View citing articles Show Details

With water

Ambient temperature; Yield given;

Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi

Tetrahedron, 1990 , vol. 46, # 21 p. 7539 - 7555 Title/Abstract Full Text View citing articles Show Details

33

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Rx-ID: 2899236 Find similar reactions

66.4%

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Bunce, Richard A.; Dowdy, Eric D.

Synthetic Communications, 1990 , vol. 20, # 19 p. 3007 - 3014 Title/Abstract Full Text Show Details

in tetrahydrofuran; hexane

0.166667 h; Heating;

34

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Rx-ID: 21234543 Find similar reactions

Multi-step reaction with 2 steps 1: 1.) trifluoromethanesulfonic acid (TFSA) / 1.) CH2Cl2, -40 deg C, 5 min, 2.) -78 deg C to 20 deg C 2: H2O, trifluoromethanesulfonic acid (TFSA) View Scheme

Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi

Journal of Organic Chemistry, 1989 , vol. 54, # 4 p. 733 - 734 Title/Abstract Full Text View citing articles Show Details


Multi-step reaction with 2 steps 1: 1) trifluoromethanesulfonic acid / 1) CH2Cl2, -40 deg C, 2) -78 deg C up to r.t. 2: H2O / Ambient temperature View Scheme

Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi

Tetrahedron, 1990 , vol. 46, # 21 p. 7539 - 7555 Title/Abstract Full Text View citing articles Show Details

35

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Rx-ID: 21274124 Find similar reactions

Multi-step reaction with 2 steps 1: 1.) trifluoromethanesulfonic acid (TFSA) / 1.) CH2Cl2, -40 deg C, 5 min, 2.) -78 deg C to 20 deg C 2: H2O, trifluoromethanesulfonic acid (TFSA) View Scheme

Okabe, Kazuaki; Ohwada, Tomohiko; Ohta, Toshiharu; Shudo, Koichi

Journal of Organic Chemistry, 1989 , vol. 54, # 4 p. 733 - 734 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 1) trifluoromethanesulfonic acid / 1) CH2Cl2, -40 deg C, 2) -78 deg C up to r.t. 2: H2O / Ambient temperature View Scheme

Ohwada, Tomohiko; Okabe, Kazuaki; Ohta, Toshiharu; Shudo, Koichi

Tetrahedron, 1990 , vol. 46, # 21 p. 7539 - 7555 Title/Abstract Full Text View citing articles Show Details

36

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70 % Chromat.

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Rx-ID: 7161698 Find similar reactions

Dormond, Alain; Elbouadili, Abdelaziz; Moise, Claude

Journal of Organic Chemistry, 1989 , vol. 54, # 15 p. 3747 - 3748 Title/Abstract Full Text View citing articles Show Details

in pentane

0.0833333 h;

A

37

B

C


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Rx-ID: 3737428 Find similar reactions

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A: 6% B: 5% C: 72%

With ytterbium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide

4.33333 h; Ambient temperature;

Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi

Journal of the Chemical Society, Chemical Communications, 1988 , # 10 p. 668 - 670 Title/Abstract Full Text View citing articles Show Details

A: 6% B: 5% C: 72%

With ytterbium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide

4.33333 h; Ambient temperature;

Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi

Journal of the Chemical Society, Chemical Communications, 1988 , # 10 p. 668 - 670 Title/Abstract Full Text View citing articles Show Details

With ytterbium

1.) THF, HMPA, RT, 2.) RT, 4 h; Yield given. Multistep reaction. Yields of byproduct given;

Hou, Zhaomin; Takamine, Kan; Aoki, Osamu; Shiraishi, Hiroyuki; Fujiwara, Yuzo; Taniguchi, Hiroshi

Journal of Organic Chemistry, 1988 , vol. 53, # 26 p. 6077 - 6084 Title/Abstract Full Text View citing articles Show Details

A

B

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Synthesize Find similar

38

Synthesize Find similar Rx-ID: 26420838 Find similar reactions

With hydrogenchloride

reaction of Cp2TiOC(CPh2)CH2 with anhydrous HCl;

Ho, Suzzy C.; Hentges, S.; Grubbs, Robert H.

Organometallics, 1988 , vol. 7, p. 780 - 782 Full Text View citing articles Show Details

39

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Rx-ID: 1698852 Find similar reactions

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Synthesize Find similar

With formic acid ethyl ester

1.) ether, 2 h, 2.) ether, 2 h; Yield given. Multistep reaction;

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Lapkin, I. I.; Kolbina, N. M.; Tatarenko, O. I.; Prokhorova, T. S.; Gartman, G. A.

Pharmaceutical Chemistry Journal, 1987 , vol. 21, # 11 p. 778 - 779 Khimiko-Farmatsevticheskii Zhurnal, 1987 , vol. 21, # 11 p. 1326 - 1328 Title/Abstract Full Text View citing articles Show Details


40

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94%

Synthesize Find similar

Rx-ID: 2827038 Find similar reactions

With hydrogenchloride in tetrahydrofuran; water

48 h; Ambient temperature;

Syper, Ludwik

Tetrahedron, 1987 , vol. 43, # 12 p. 2853 - 2872 Title/Abstract Full Text View citing articles Show Details

A

B

C

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Synthesize Find similar

Synthesize Find similar

41

Synthesize Find similar Rx-ID: 2979966 Find similar reactions

A: 97 % Spectr.

With potassium superoxide in acetonitrile

T=-30°C; 9 h;

Kim, Yong Hae; Lee, Hyeon Kyu; Chang, Hae Sung

Tetrahedron Letters, 1987 , vol. 28, # 37 p. 4285 - 4288 Title/Abstract Full Text View citing articles Show Details

42

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Rx-ID: 3858729 Find similar reactions

Synthesize Find similar

1.) ether,heating,2h, 2.) heating, 2h; Yield given. Multistep reaction;

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Synthesize Find similar

Lapkin, I. I.; Kolbina, N. M.; Tatarenko, O. I.

Journal of Organic Chemistry USSR (English Translation), 1987 , vol. 23, # 2 p. 279 - 281 Zhurnal Organicheskoi Khimii, 1987 , vol. 23, # 2 p. 315 - 317 Title/Abstract Full Text Show Details


43

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Synthesize Find similar

Rx-ID: 1992816 Find similar reactions

With hydrogenchloride in methanol

Ambient temperature;

Kitamura, Tsugio; Kobayashi, Shinjiro; Taniguchi, Hiroshi

Journal of the American Chemical Society, 1986 , vol. 108, # 10 p. 2641 - 2645 Title/Abstract Full Text View citing articles Show Details

44

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87 % Chromat.

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Rx-ID: 3662653 Find similar reactions

With tetrachloromethane; bis-maleimidodiphenyl-methane acid

T=200°C; 1 h;

Shimizu, Nobujiro; Yamaoka, Shintaro; Tsuno, Yuho

Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 12 p. 3853 - 3854 Title/Abstract Full Text Show Details

45

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Synthesize Find similar

Rx-ID: 294189 Find similar reactions

80%

With sulfuric acid in dichloromethane

T=25°C; 0.25 h;

Kanemoto, Shigekazu; Morizawa, Yoshitomi; Oshima, Koichiro; Nozaki, Hitosi

Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 12 p. 3941 - 3942 Title/Abstract Full Text Show Details

With sulfuric acid

McKenzie; Roger

Journal of the Chemical Society, 1924 , vol. 125, p. 851 Full Text Show Details

v. Auwers; Mauss

Biochemische Zeitschrift, 1928 , vol. 192, p. 222 Full Text Show Details

Tiffeneau; Dorlencourt

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906 , vol. 143, p. 127; 651 Anm.


Annales de Chimie (Cachan, France), 1909 , vol. <8> 16, p. 256 Full Text Show Details

Rack

Chemische Berichte, 1923 , vol. 56, p. 1130 Full Text Show Details

With hydrogenchloride

T=180°C;

Stoermer

Chemische Berichte, 1906 , vol. 39, p. 2302 Full Text Show Details

Hide Details

With hydrogenchloride

T=180°C;

Smith; Hoehn

Journal of the American Chemical Society, 1941 , vol. 63, p. 1184,1186 Full Text View citing articles Show Details

With sulfuric acid

T=150°C;

Wittig; Gauss

Chemische Berichte, 1947 , vol. 80, p. 363,373 Full Text View citing articles Show Details

46

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Rx-ID: 1703123 Find similar reactions

87%

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Synthesize Find similar

Huszthy, Peter; Lempert, Karoly; Simig, Gyula; Tamas, Jozsef

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982 , p. 1671 - 1674 Title/Abstract Full Text View citing articles Show Details

in tetrahydrofuran

5 h; Heating;

A

B

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Synthesize Find similar

47

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A: 24% B: 72%

With Et2AlSPh in hexane

T=25°C; 0.2 h; Title compound not separated from byproducts;

Kanemoto, Shigekazu; Morizawa, Yoshitomi; Oshima, Koichiro; Nozaki, Hitosi

Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 12 p. 3941 - 3942 Title/Abstract Full Text Show Details

A: 24%

With Et2AlSPh in hexane

Kanemoto, Shigekazu; Morizawa, Yoshitomi; Oshima, Koichiro; Nozaki, Hitosi


B: 72%

Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 12 p. 3941 - 3942 Title/Abstract Full Text Show Details

T=25°C; 0.2 h; Title compound not separated from byproducts;

48

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100%

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Rx-ID: 2571125 Find similar reactions

With Dowex 50W ion-exchange resin in dichloromethane

Heating;

Johnson, Carl R.; Bade, Thomas R.

Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1205 - 1212 Title/Abstract Full Text View citing articles Show Details

49

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Synthesize Find similar

Rx-ID: 21275887 Find similar reactions

Multi-step reaction with 2 steps 1: 1.) LDA / 1.) THF, hexane, -80 deg C, 5 min, 2.) from -80 deg C to room temp. 2: 100 percent / Dowex 50W ion-exchange resin / CH2Cl2 / Heating View Scheme

Johnson, Carl R.; Bade, Thomas R.

Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1205 - 1212 Title/Abstract Full Text View citing articles Show Details

A

B

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Synthesize Find similar

50

Synthesize Find similar Rx-ID: 2956468 Find similar reactions

With DCNB Irradiation;

Majima, Tetsuro; Pac, Chyongjin; Sakurai, Hiroshi

Journal of the American Chemical Society, 1980 , vol. 102, # 16 p. 5265 - 5273 Title/Abstract Full Text View citing articles Show Details


51

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Synthesize Find similar

Rx-ID: 20529184 Find similar reactions

Multi-step reaction with 2 steps 1: 92 percent / diethyl ether / 3 h 2: DCNB / Irradiation View Scheme

Majima, Tetsuro; Pac, Chyongjin; Sakurai, Hiroshi

Journal of the American Chemical Society, 1980 , vol. 102, # 16 p. 5265 - 5273 Title/Abstract Full Text View citing articles Show Details

52

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Rx-ID: 847535 Find similar reactions

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With aluminium trichloride

Golowjaschkina; Zukerwanik

Doklady Akademii Nauk UzSSR, 1958 , # 2 p. 31 Chem.Abstr., 1959 , p. 17051 Full Text Show Details

A

B

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Synthesize Find similar

53

Synthesize Find similar Rx-ID: 554259 Find similar reactions

T=90°C; Zersetzung; Rate constant;

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Pritzkow

Chemische Berichte, 1955 , vol. 88, p. 572,576,579 Full Text Show Details


A

B

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Synthesize Find similar

54

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Synthesize Find similar

Synthesize Find similar

Rx-ID: 554573 Find similar reactions

Pritzkow

Chemische Berichte, 1955 , vol. 88, p. 572,576,579 Full Text Show Details

T=80°C; Zersetzung; Rate constant;

A

B

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Synthesize Find similar

55

Synthesize Find similar

Synthesize Find similar

Rx-ID: 663270 Find similar reactions

Pritzkow

Chemische Berichte, 1955 , vol. 88, p. 572,576,579 Full Text Show Details

T=90°C; Zersetzung; Rate constant;

A

B

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Synthesize Find similar

56

Synthesize Find similar Rx-ID: 713149 Find similar reactions

T=90°C; Zersetzung; Rate constant;

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Pritzkow

Chemische Berichte, 1955 , vol. 88, p. 572,576,579 Full Text Show Details


A

B

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Synthesize Find similar

57

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Synthesize Find similar

Rx-ID: 848265 Find similar reactions

Pritzkow

Chemische Berichte, 1955 , vol. 88, p. 572,576,579 Full Text Show Details

T=90°C; Zersetzung; Rate constant;

58

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Rx-ID: 104447 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Winstein; Marshall

Journal of the American Chemical Society, 1952 , vol. 74, p. 1120,1126 Full Text Show Details

59

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Synthesize Find similar

Rx-ID: 7161703 Find similar reactions

Jilek; Protiva

Chemicke Listy, 1950 , vol. 44, p. 49 Chem.Abstr., 1951 , p. 7987 Full Text Show Details


60

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Synthesize Find similar

Rx-ID: 7161699 Find similar reactions

With pumice stone; thorium(IV) dioxide; acetic acid

T=450°C;

Haarmann and Reimer

Patent: DE825085 , 1949 ; DRP/DRBP Org.Chem. Full Text Show Details

61

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Rx-ID: 7161701 Find similar reactions

With Neutral lead acetate

T=280°C;

Adkins et al.

Journal of the American Chemical Society, 1949 , vol. 71, p. 3622,3623 Full Text View citing articles Show Details

62

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With zinc(II) chloride

T=330°C; anschliessend Behandeln mit Wasser;

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Rx-ID: 309118 Find similar reactions

Saleskaja

Zhurnal Obshchei Khimii, 1948 , vol. 18, p. 1172,1176 Chem.Abstr., 1949 , p. 1753 Full Text Show Details


63

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Synthesize Find similar

Rx-ID: 7981568 Find similar reactions

Saleskaja

Zhurnal Obshchei Khimii, 1948 , vol. 18, p. 1172,1176 Chem.Abstr., 1949 , p. 1753 Full Text Show Details

T=330°C; anschliessend Behandeln mit Wasser;

64

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Synthesize Find similar

Rx-ID: 104458 Find similar reactions

With diethyl ether; NaCH(COOEt)2

man kocht das Produkt mit Salzsaeure;

Neuberg; Ohle

Biochemische Zeitschrift, 1922 , vol. 127, p. 338 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: diethyl ether; N.N-dimethyl-aniline 2: KNH2; liquid ammonia / Erhitzen der von Ammoniak befreiten Reaktionsloesung unter Einleiten von Stickstoff, anschliessend Behandeln mit Acetylchlorid, zuletzt bei Siedetemperatur, und Erhitzen mit Toluol-sulfonsaeure-(4)monohydrat in Benzol View Scheme

Yost; Hauser

Journal of the American Chemical Society, 1947 , vol. 69, p. 2325,2327 Full Text Show Details

65

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Rx-ID: 749967 Find similar reactions

With ammonia; KNH2

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Synthesize Find similar

Yost; Hauser


Journal of the American Chemical Society, 1947 , vol. 69, p. 2325,2327 Full Text Show Details

Erhitzen der von Ammoniak befreiten Reaktionsloesung unter Einleiten von Stickstoff, anschliessend Behandeln mit Acetylchlorid, zuletzt bei Siedetemperatur, und Erhitzen mit Toluol-sulfonsaeure-(4)-monohydrat in Benzol;

66

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Synthesize Find similar

Rx-ID: 7161695 Find similar reactions

With aluminium trichloride

Ruggli; Dahn; Wegmann

Helvetica Chimica Acta, 1946 , vol. 29, p. 113,118 Full Text Show Details

A

B

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67

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Synthesize Find similar

Rx-ID: 5525891 Find similar reactions

Hoch

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1934 , vol. 198, p. 1865,1866 Full Text Show Details

Campbell et al.

Journal of Organic Chemistry, 1943 , vol. 8, p. 103,107 Full Text Show Details

A

B

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Synthesize Find similar

68

Synthesize Find similar Rx-ID: 5525892 Find similar reactions

Synthesize Find similar


Hoch

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1934 , vol. 198, p. 1865,1866 Full Text Show Details

Campbell et al.

Journal of Organic Chemistry, 1943 , vol. 8, p. 103,107 Full Text Show Details

69

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Synthesize Find similar

Rx-ID: 7161696 Find similar reactions

With aluminium trichloride

Richard

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1935 , vol. 200, p. 753 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1942 , vol. 214, p. 673 Full Text Show Details

70

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Rx-ID: 7161697 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Synthesize Find similar

Richard

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1935 , vol. 200, p. 753 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1942 , vol. 214, p. 673 Full Text Show Details

71

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With hydrogenchloride

Rx-ID: 7161691 Find similar reactions

Hoch


Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1934 , vol. 198, p. 1865,1866 Full Text Show Details

72

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Synthesize Find similar

With sulfuric acid

T=140 - 145°C;

Rx-ID: 293550 Find similar reactions

Bardan

Bulletin de la Societe Chimique de France, 1931 , vol. <4> 49, p. 1875,1879 Full Text Show Details

73

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Rx-ID: 7161692 Find similar reactions

With diethyl ether; iodine; mercury(II) oxide

Behandeln des in Aether geloesten Reaktionsprodukts mit wss. AgNO3-Loesung;

Tiffeneau; Levy

Bulletin de la Societe Chimique de France, 1931 , vol. <4> 49, p. 1806,1811 Full Text Show Details

74

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Rx-ID: 7161694 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Bardan

Bulletin de la Societe Chimique de France, 1931 , vol. <4> 49, p. 1875,1879 Full Text Show Details


75

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Rx-ID: 7161700 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Synthesize Find similar

Tiffeneau; Levy

Bulletin de la Societe Chimique de France, 1931 , vol. <4> 49, p. 1806,1811 Full Text Show Details

Behandlung des Reaktionsprodukts mit wss. AgNO3-Loesung; 1.2-diphenyl-propene-(1);

76

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Rx-ID: 7161693 Find similar reactions

With acetic acid; sodium nitrite

McKenzie; Roger

Journal of the Chemical Society, 1924 , vol. 125, p. 851 Full Text Show Details

McKenzie; Richardson

Journal of the Chemical Society, 1923 , vol. 123, p. 89 Full Text Show Details

McKenzie; Mills

Chemische Berichte, 1929 , vol. 62, p. 1789 Full Text Show Details

77

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Synthesize Find similar

Multi-step reaction with 2 steps 1: diethyl ether / man zersetzt das Reaktionsprodukt mit verd. Essigsaeure 2: sulfuric acid View Scheme

Rx-ID: 22063251 Find similar reactions

Tiffeneau; Dorlencourt

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906 , vol. 143, p. 127; 651 Anm. Annales de Chimie (Cachan, France), 1909 , vol. <8> 16, p. 256 Full Text Show Details


Multi-step reaction with 2 steps 2: sulfuric acid View Scheme

v. Auwers; Mauss Biochemische Zeitschrift, 1928 , vol. 192, p. 222 Full Text Show Details

Multi-step reaction with 2 steps 2: sulfuric acid View Scheme

v. Auwers; Mauss Biochemische Zeitschrift, 1928 , vol. 192, p. 222 Full Text Show Details

78

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Rx-ID: 7161690 Find similar reactions

Lagrave

Annales de Chimie (Cachan, France), 1927 , vol. <10> 8, p. 392 Full Text View citing articles Show Details

Levy; Lagrave

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1925 , vol. 180, p. 1034 Full Text Show Details

bei Destillation;

79

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Synthesize Find similar

Rx-ID: 388601 Find similar reactions

With sulfuric acid

Thomas; Bettzieche

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1924 , vol. 140, p. 239 Chemische Berichte, vol. 146, p. 233 Full Text Show Details

With hydrogenchloride

Bettzieche

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1926 , vol. 161, p. 188 Full Text Show Details

Thomas; Bettzieche

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1924 , vol. 140, p. 239 Chemische Berichte, vol. 146, p. 233 Full Text Show Details

With sulfuric acid

Bettzieche

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1926 , vol. 161, p. 188 Full Text Show Details

Thomas; Bettzieche

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1924 , vol. 140, p. 239 Chemische Berichte, vol. 146, p. 233 Full Text Show Details


80

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Synthesize Find similar

Rx-ID: 492065 Find similar reactions

Staudinger; Rheiner

Helvetica Chimica Acta, 1924 , vol. 7, p. 9 Full Text Show Details

81

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Synthesize Find similar

With sulfuric acid

Rx-ID: 407508 Find similar reactions

Stoermer

Chemische Berichte, 1906 , vol. 39, p. 2302 Full Text Show Details

82

Synthesize Find similar durch Oxydation;

Rx-ID: 7161702 Find similar reactions

Tiffeneau; Dorlencourt

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906 , vol. 143, p. 127; 651 Anm. Annales de Chimie (Cachan, France), 1909 , vol. <8> 16, p. 256 Full Text Show Details


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