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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 12
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Original Articles

Cohalogenation of Alkenes: A New Base Induced Fragmentation Reaction of β, δ'-Dihalogenated Ethers to Oxiran and Butadiene. Indirect Oxygen Atom Transfer from THF

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Pages 1893-1898 | Received 13 Apr 1990, Published online: 24 Oct 2006

References

  • Rodriguez , J. , Dulcere , J. P. and Bertrand , M. 1984 . Tetrahedron Letters , 25 : 527
  • Rodriguez , J. , Dulcère , J. P. and Bertrand , M. 1983 . ibid. , 24 : 4423
  • Dinulescu , I. G. , Avram , M. , Jijovici , C. T. , Farcasiu , M. and Nenitzescu , C. D. 1964 . Chem. and Ind. , : 840 Bertrand, M.; Dulcère, J. P.; Rodriguez, J. and Zahra, J. P., Tetrahedron Letters, 1983, 24, 1967
  • Oxirans were characterized by comparison of their spectral datas with authentical samples
  • Compound 8 is obtained as a 75/25 mixture of trans/cis isomers; IR (neat) 3030; 1655; 1090; 965 cm−1; 1H NMR (60 MHz, CDCI3) δ 1.5–2.2 (m, 9H); 3.6–4.1 (m, 3H); 5.4–5.6 (m, 2H); 5.68 (s, 2H); 13C NMR (100 MHz, CDCI3)δ 17.8; 19.3; 25.3; 28.5; 68.8; 71.9; 127.9; 128.2; 130.7; Anal. Calcd. for C10H16: C, 88.2; H, 11.8; Found: C, 88.31; H, 11.70
  • Hubert , A. J. and Reimlinger , M. 1969 . Synthesis , : 97
  • Rodriguez , J. 1984 . Thesis , Marseille, , France : Faculté des Sciences et Techniques de Saint-Jérome .

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