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5832118Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle [url=http://www.ourexperiment.org/racemic_pzq/567]see [b]MW45-1[/b][/url] [data=size:500x180]395[/data] [b]Hazard and Risk Assessment:[/b] Reaction Class: 2 Hazards: T toxic Risk rating: U = Unlikely Start time: 1:00 PM 03/08/2010 End time: 2:20 PM 03/08/2010 [b]Procedure:[/b] [2] [url=http://www.ourexperiment.org/racemic_pzq/567][b]MW45-1[/b][/url] (500 mg, 1.09 mmol) was placed in a roundbottom flask and heated in a heating mantle to 250°C for 80 min. The dark brown solid was dissolved in chloroform and purified by column chromatography (silica gel, CHCl3; 100%). [b]References:[/b] [url=http://dx.doi.org/10.1021/ja806875c][1] “Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid−Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction”, M. Hatano, T. Maki, K. Moriyama, M. Arinobe and K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858–16860; DOI: 10.1021/ja806875c. [/url] [url=http://www3.interscience.wiley.com/journal/122382952/abstract][2] “A Powerful Chiral Counteranion Motif for Asymmetric Catalysis”, P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363 –4366; DOI: 10.1002/anie.200901768.[/url] See following experiment: [*] [url=http://www.ourexperiment.org/racemic_pzq/587]Preparation of 1,1’-Binaphthalene-2,2’-disulfonic acid (MW45-3)[/url] [b]Procedure from the reference:[/b] [2] [i](R)-3,3'-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl-S,S'-bis(N,N-dimethylthiocarbamate) (13):[/i] O-Thiocarbamate 12 (2.31 g, 2.61 mmol) was placed into a dram glass vial under argon and heated in a metal block to 250 °C for 80 min. The resulting crude product was purified by column chromatography using hexanes/ethyl acetate (95/5) as eluent to afford 13 (2.19 g, 95% yield).]]>
1. step: preparation of the starting material -> see MW45-1

Reaction Scheme


Hazard and Risk Assessment:
Reaction Class: 2
Hazards: T toxic
Risk rating: U = Unlikely

Start time: 1:00 PM 03/08/2010
End time: 2:20 PM 03/08/2010

Procedure: [2]
MW45-1 (500 mg, 1.09 mmol) was placed in a roundbottom flask and heated in a heating mantle to 250°C for 80 min. The dark brown solid was dissolved in chloroform and purified by column chromatography (silica gel, CHCl3; 100%).

References:
[1] “Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid−Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction”, M. Hatano, T. Maki, K. Moriyama, M. Arinobe and K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858–16860; DOI: 10.1021/ja806875c.

[2] “A Powerful Chiral Counteranion Motif for Asymmetric Catalysis”, P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363 –4366; DOI: 10.1002/anie.200901768.

See following experiment:
  • Preparation of 1,1’-Binaphthalene-2,2’-disulfonic acid (MW45-3)

    Procedure from the reference:
  • [2]
    (R)-3,3'-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl-S,S'-bis(N,N-dimethylthiocarbamate) (13):
    O-Thiocarbamate 12 (2.31 g, 2.61 mmol) was placed into a dram glass vial under argon and heated in a metal block to 250 °C for 80
    min. The resulting crude product was purified by column chromatography using hexanes/ethyl acetate (95/5) as eluent to afford 13 (2.19 g, 95% yield).
    ]]>2010-08-03T09:28:43+01:002011-05-25T06:24:59+01:00622876935bd31bb2e455720e760dd227chttps://www.ourexperiment.org/data/395.xmlhttps://www.ourexperiment.org/data/401.xmlhttps://www.ourexperiment.org/data/403.xmlhttps://www.ourexperiment.org/data/406.xmlhttps://www.ourexperiment.org/data/409.xmlhttp://www.ourexperiment.org/uri/4ehttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.htmlhttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.htmlhttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xmlhttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.pnghttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=583https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=584https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=585https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=586https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=594https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=595https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=596https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=597https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=598https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=2118https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=701213Re: Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)ErrorRe: Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)yield and NMR of product missingyield and NMR of product missing2010-09-06T20:09:17+01:00
    5837012Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)
    Experiments
    profiles.google.com-micha.wolfleMichael Wolfle [url=http://www.ourexperiment.org/racemic_pzq/567]see [b]MW45-1[/b][/url] [data=size:500x180]395[/data] [b]Hazard and Risk Assessment:[/b] Reaction Class: 2 Hazards: T toxic Risk rating: U = Unlikely Start time: 1:00 PM 03/08/2010 End time: 2:20 PM 03/08/2010 [b]Procedure:[/b] [2] [url=http://www.ourexperiment.org/racemic_pzq/567][b]MW45-1[/b][/url] (500 mg, 1.09 mmol) was placed in a roundbottom flask and heated in a heating mantle to 250°C for 80 min. The dark brown solid was dissolved in chloroform and purified by column chromatography (silica gel, CHCl3; 100%). [b]References:[/b] [url=http://dx.doi.org/10.1021/ja806875c][1] “Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid−Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction”, M. Hatano, T. Maki, K. Moriyama, M. Arinobe and K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858–16860; DOI: 10.1021/ja806875c. [/url] [url=http://www3.interscience.wiley.com/journal/122382952/abstract][2] “A Powerful Chiral Counteranion Motif for Asymmetric Catalysis”, P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363 –4366; DOI: 10.1002/anie.200901768.[/url] See following experiment: [*] [url=http://www.ourexperiment.org/racemic_pzq/587]Preparation of 1,1’-Binaphthalene-2,2’-disulfonic acid (MW45-3)[/url] [b]Procedure from the reference:[/b] [2] [i](R)-3,3'-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl-S,S'-bis(N,N-dimethylthiocarbamate) (13):[/i] O-Thiocarbamate 12 (2.31 g, 2.61 mmol) was placed into a dram glass vial under argon and heated in a metal block to 250 °C for 80 min. The resulting crude product was purified by column chromatography using hexanes/ethyl acetate (95/5) as eluent to afford 13 (2.19 g, 95% yield).]]>
    1. step: preparation of the starting material -> see MW45-1

    Reaction Scheme


    Hazard and Risk Assessment:
    Reaction Class: 2
    Hazards: T toxic
    Risk rating: U = Unlikely

    Start time: 1:00 PM 03/08/2010
    End time: 2:20 PM 03/08/2010

    Procedure: [2]
    MW45-1 (500 mg, 1.09 mmol) was placed in a roundbottom flask and heated in a heating mantle to 250°C for 80 min. The dark brown solid was dissolved in chloroform and purified by column chromatography (silica gel, CHCl3; 100%).

    References:
    [1] “Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid−Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction”, M. Hatano, T. Maki, K. Moriyama, M. Arinobe and K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858–16860; DOI: 10.1021/ja806875c.

    [2] “A Powerful Chiral Counteranion Motif for Asymmetric Catalysis”, P. García-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem. Int. Ed. 2009, 48, 4363 –4366; DOI: 10.1002/anie.200901768.

    See following experiment:
  • Preparation of 1,1’-Binaphthalene-2,2’-disulfonic acid (MW45-3)

    Procedure from the reference:
  • [2]
    (R)-3,3'-Bis[3,5-bis(trifluoromethyl)phenyl]-1,1'-binaphthyl-2,2'-diyl-S,S'-bis(N,N-dimethylthiocarbamate) (13):
    O-Thiocarbamate 12 (2.31 g, 2.61 mmol) was placed into a dram glass vial under argon and heated in a metal block to 250 °C for 80
    min. The resulting crude product was purified by column chromatography using hexanes/ethyl acetate (95/5) as eluent to afford 13 (2.19 g, 95% yield).
    ]]>2010-08-03T09:28:43+01:002015-05-01T02:37:56+01:006https://www.ourexperiment.org/data/395.xmlhttps://www.ourexperiment.org/data/401.xmlhttps://www.ourexperiment.org/data/403.xmlhttps://www.ourexperiment.org/data/406.xmlhttps://www.ourexperiment.org/data/409.xmlhttp://www.ourexperiment.org/uri/4ehttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.htmlhttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.htmlhttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xmlhttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.pnghttps://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=583https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=584https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=585https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=586https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=594https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=595https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=596https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=597https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=598https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=2118https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=7012https://www.ourexperiment.org/racemic_pzq/583/Preparation_of_11Binaphthalene22diylSSbisNNdimethylthiocarbamate_MW452.xml?revision=-113Re: Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)ErrorRe: Preparation of 1,1’-Binaphthalene-2,2’-diyl-S,S’-bis(N,N’-dimethylthiocarbamate) (MW45-2)yield and NMR of product missingyield and NMR of product missing2010-09-06T20:09:17+01:00