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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 4
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Original Articles

Improved Method of Dibromocyclopropane Derivatives Synthesis in Catalytic Two-Phase Reaction

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Pages 305-309 | Received 09 Jul 1973, Published online: 05 Dec 2006

References

  • Makosza , K. and Wawrzyniewicz , M. 1969 . Tetrahedron Letters , : 4659
  • Dehlow , E. V. 1971 . Tetrahedron , 27 : 4071 For example:, ibid., 28, 175(1972); W.P. Weber and G.W. Gokel, Tedrahedron Letters; 1972 1637; G.C. Joshi, N. Singh and L.Y. Pande, ibid., 1972, 1461; I. Tabuahi, Z. Yoshida and N. Takahashi, J. Amer. Chem. Soc., 93, 1820 (1971)
  • Makosza , M. and Fedoryńki , M. 1971 . Bull. Acad. Polon., Ser. Sci. Chim. , 19 : 105 B. V. Dehmlow and J. Schönefeld, Ann., 744, 42 (1971)
  • Makosta , M. and Białecka , E. 1971 . Tetrahedron Letters , : 4517
  • Weyerstahl , P. , Blums , G. and Müller , C. 1971 . ibid. , : 3869
  • Weyerstahl , P. , Mathias , R. and Blume , G. 1973 . ibid. , : 611
  • Skatteb⊘l , L. , Abnkhnroun , G. A. and Greibrokk , T. 1973 . ibid. , : 1367
  • NMR H1 spectra of new compounds (room temperature, CCl4 as a solvent, TMS as a internal standart, δ values): 1, 1-dibromo-2-n-butoxycyclopropane: triplet 0,95 (3H, J=6 Hz), multiplets 1,15–1, 93 (6H), 3,30–3,90 (3H). 1,1-dibromo-2,2-dimethyl-3-chloromethyl cyclopropane: 2 singlets 1,30 and 1,45 (2×3H), triplet 1,68 (1H, J=7,5 Hz), multiplet 3,25-3,92 (2H). n-Butyl 1-methyl-2,2-dibromocyclopropanecarboxylate: triplet 0,95 (3H, J=6 Hz), singlet 1,55 (3H), multiplet 1,1–2,0 (5H), two signals 2,25 and 2,38 (1H) - one of cyclopropane ring protons (the second one is overlaped by multiplet), triplet 4,13 (2H, J=6 Hz). (1, I=dibrmo-2,2-dimethyl) cyclopropylmethyl acetate: 2 singlets 1,25 and 1,40 (2×3H), triplet 1,58 (1H, J=7,5 Hz], singlet 2, OO (3H), dublet 4,05 (2H, J=7,5 Hz)
  • Srell , P. S. and Garner , A. Y. 1956 . J. Amer. Chem. Soc. , 78 : 5430
  • Doering , W. E. and Henderson , W. A. 1958 . ibid. , 80 : 5274
  • Dale , W. J. and Swartzentruber , P. E. 1959 . J. Org. Chem. , 2 : 955
  • The product is unstable at room temperature, distillation at higher temp. results in decomposition
  • Despite rather wide temp. range the product is obtained in pure state (GLC)
  • The reaction was carried out at temp. below 30°C

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