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Polyenic compounds communication 1. Synthesis of 1,5-diaryl-1,3,5-hexatrienes

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    Phenyllithium and 1-naphthyllithium undergo 1,2-addition to the conjugated system of 3-methyl-6-phenyl-3, 5-hexadien-2-one with formation of the corresponding tertiary alcohols, which give arylhexatrienes by further reaction, on the other hand, 9- fluorenyllithium undergoes 1, 6-addition with this ketone with formation of the un saturated ketone 6 -fluorenyl-3-methyl-6-phenyl-5 -hexen-2 -one.

  2. 2.

    By the dehydration of 3-methyl-2,6-diphenyl-3,5-hexadien-2-ol, four stereoisomeric 4-methyl-1,5 diphenyl-1, 3,5-hexatrienes can be prepared.

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Literature cited

  1. H. Halmssler and C. Brugger, Ber. 77B, 152 (1944).

    Google Scholar 

  2. F. Straus, Ann. 342, 262 (1905).

    Google Scholar 

  3. J. H. Pinckard, B. Wille and L. Zechmeister, J. Am. Chem. Soc. 70, 1938 (1948).

    Google Scholar 

  4. K. Lunde and L. Zechmeister, J. Am. Chem. Soc. 76, 2308 (1954).

    Google Scholar 

  5. C. P. Koelsch and H. J. Richter, J. Org. Chem. 473 (1938)

  6. S. H. Tucker and M. Whalley, J. Chem. Soc. 1949, 50.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry of the Academy of Sciences of the USSR, USSR

    B. M. Mikhailov & G. S. Ter-Sarkisyan

Authors
  1. B. M. Mikhailov
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  2. G. S. Ter-Sarkisyan
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Mikhailov, B.M., Ter-Sarkisyan, G.S. Polyenic compounds communication 1. Synthesis of 1,5-diaryl-1,3,5-hexatrienes. Russ Chem Bull 5, 1095–1099 (1956). https://doi.org/10.1007/BF01177362

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  • DOI: https://doi.org/10.1007/BF01177362

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