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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 14
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Original Articles

Synthesis of Some 3-Substituted-2,4-dimethyl-1,3-pentadienes1

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Pages 1341-1347 | Published online: 06 Dec 2006

References

  • This work was supported, in part, by the Iowa State University Research Foundation.
  • Halazy , S. and Krief , A. 1997 . Tetrahedron Lett. , : 1980 and references therein.
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  • Warner , P. , Chang , S.-C. , Powell , D. R. , Jacodson , R. A. , Warner , P. , Chang , S.-C. , Powell , D. R. and Jacobson , R. A. 1981 . Tetrahedron Lett. , 102 : 5125 J. Am. Chem. Soc. 1980, 533
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  • The efficacy of Cu turnings should be emphasized. Thus, pyrolysis of 1 in a glass helices packed column at 300[ddot]C gave a 1:2 ratio of 3a and 3-bromo-2,4-dimethylpent-2-ene-4-ol, and a 1:1 ratio of these two products at 400[ddot]C When the column was packed with quartz chips, the above two products formed in a 1:1.4 ratio at 500[ddot]C; only at 600[ddot]C did 3a become the sole product. With 2b, pyrolysis through glass helices at 300[ddot]C produced a 3:1:2 ratio of starting material, desired 3b, and a dimer of 3b; at 600[ddot]C with quartz chips, the products were a 1:2 mixture of 3b and its dimer.
  • Skell , P. S. and Garner , A. Y. 1956 . J. Am. Chem. Soc. , 78 : 5430 These authors report a 54% yield of 1
  • Hiyama , T. , Takehara , S. , Kitatani , K. and Nozaki , H. 1974 . Tetrahedron Lett. , 3295.
  • Vogel , E. and Ginsburg , D. 1975 . Propellanes , 119 Weinheim : Verlag Chemie . unpublished results, quoted in
  • Bushby , R. J. 1975 . J. Chem. Soc., Perkin Trans. I , 2513.
  • Dai , S.-H. and Dolbier , W. R. Jr. 1972 . J. Org. Chem. , 37 : 950
  • Gramenitskaya , V. N. , Vodka , V. S. , Golovkina , L. S. and Vulfson , N. S. 1977 . Zh. Org. Khim. , 13 : 2329
  • Pellicciari , R. , Sisani , E. and Fringuelli , R. 1980 . Tetrahedron Lett. , 4039.

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