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Quinquiphenyl and Sexiphenyl

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Polycyclic Hydrocarbons
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Abstract

Quinquiphenyl and other polyphenyls are formed by reduction of benzenediazonium sulphate in concentrated sulphuric acid and acetic acid with formic acid and copper powder.1 A mixture of 4-iododiphenyl, 4-iodoterphenyl and silver powder gives quinquiphenyl.1 4-Diphenyl lithium and cyclohexanedione yield the diol (I). This is easily dehydrated to the dihydro compound (II) which is dehydrogenated to quinquiphenyl by heating with selenium. Even contact with air achieves dehydrogenation.2

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References

  1. Gerngross, O. and Dunkel, M., Ber. dtsch. cher. Ges. 57, 730 (1924); Gern-gross, O., Schachnow, C. and Jonas, R., Ber. dtsch. chem. Ges. 57, 749 (1924).

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  2. Müller, E. and Töpel, T., Ber. dtsch. chem. Ges. 72, 282 (1939).

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  3. Vorländer, D., Z. phys. Chem. 126, 471; 134, 160 (1927).

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  4. Pummerer, R. and Bittner, K., Ber. dtsch. them. Gers. 57, 84 (1924).

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  5. Pummerer, R. and Seligsberger, L., Ber. dtsch. cher. Ges. 64, 2477 (1931).

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© 1964 Springer-Verlag Berlin Heidelberg

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Clar, E. (1964). Quinquiphenyl and Sexiphenyl. In: Polycyclic Hydrocarbons. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-01668-8_13

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  • DOI: https://doi.org/10.1007/978-3-662-01668-8_13

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-01670-1

  • Online ISBN: 978-3-662-01668-8

  • eBook Packages: Springer Book Archive

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