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Synthesis of 1,2,3-Butatrienecarboxylic Acids^†

Corresponding Author

Prof. Dr. Franz W. Nader

Organisch-chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg 1 (FRG)

Organisch-chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg 1 (FRG)Search for more papers by this author

Dipl.-Chem. Claus-Dieter Wacker,

Dipl.-Chem. Claus-Dieter Wacker

Organisch-chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg 1 (FRG)

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Prof. Dr. Franz W. Nader,

Corresponding Author

Prof. Dr. Franz W. Nader

Organisch-chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg 1 (FRG)

Organisch-chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg 1 (FRG)Search for more papers by this author

Dipl.-Chem. Claus-Dieter Wacker,

Dipl.-Chem. Claus-Dieter Wacker

Organisch-chemisches Institut der Universität, Im Neuenheimer Feld 270, D-6900 Heidelberg 1 (FRG)

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First published: October 1985

https://doi.org/10.1002/anie.198508511

Citations: 10

^†

This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and BASF AG.

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The first butatrienecarboxylic acids, the triphenyl derivative 1 and the two E/Z isomeric dicarboxylic acids 2 and 3, have been prepared. Whereas 2, R¹ = tBu, is configurationally stable in solution at room temperature, 3, R¹ = Ph, isomerizes under these conditions; the E form predominates in the equilibrium (R = H).

References

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7 This synthetic concept also includes the Doehring-Moore-Skattebol method for cumulence chain extension with dihalocarbene. This method fails in the presence of carboxylic acid functions; see also K. Kratzat, F. W. Nader, T. Schwarz, Angew. Chem. 93 (1981) 611;
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15 ¹H NMR (300 MHz, CDCl₃): E- 5b: δ = 3.94 (s, 6H, OCH₃), 7.33–7.47 (m, 6H aromatic), 7.92–8.03 (m,4H, 0-H); Z-5b: δ = 3.95 (s, 6H, OCH₃), 7.34–7.48 (m, 6H, aromatic), 7.76–7.88 (m, 4H, o-H).
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16 ¹H-NMR (90 MHz, [D₆] DMSO): E-7: δ = 7.34–7.61 (m, 6H aromatic), 7.77–8.05 (m, 4H, O-H); Z-7: δ = 7.33–7.55 (m, 6H aromatic), 7.64–7.81 (m, 4H, o-H).
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Volume24, Issue10

October 1985

Pages 851-852

Synthesis of 1,2,3-Butatrienecarboxylic Acids^†

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Synthesis of 1,2,3-Butatrienecarboxylic Acids^†