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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 9
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Original Articles

A Simple Laboratory Procedure for Preparation of (1-Methylethenyl)oxirane (3,4-Epoxyisoprene)

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Pages 1287-1292 | Received 19 Jan 1990, Published online: 24 Oct 2006

References

  • Ghibri , A. , Alexakis , A. and Normant , J. F. 1985 . Tetrahedron Lett. , : 3075 Mas, J. M; Malacria, M.; Gore, J.; J. Chem. Soc., Chem. Commun., 1985, 1161; Naruta, Y.; Maruyama, K.; Chem. Lett., 1987, 963; Marshall, J. A.; Trometer, J. D.; Blough, B. E.; Crute, T. D.; J. Org. Chem., 1988, 53, 4274. See also refs. 3a, 6.
  • Eletti-Bianchi , G. , Centini , F. and Re , L. 1976 . J. Org. Chem. , 41 : 1648 Fransen, M. R.; Palings, I.; Lugtenburg, J.; Jansen, P. A. A.; Groenendijk, G. W. T.; Recl. Trav. Chim. Pays-Bas, 1980, 99 (12), 384.
  • Ledon , H. J. and Varescon , F. 1984 . Inorg. Chem. , 23 ( 18 ) : 2735 For example see:, De Carvalho, M. E.; Meunier, B.; Nouv. J. Chim., 1986, 10, 223; Banfi, S.; Montanari, F.; Penso, M.; Sosnovskikh, V.; Vigano, P.; Gazz. Chim. Ital., 187, 117, 689; Agarwal, D. D.; Shrivastava, S.; Polyhedron, 1988, 7, 2569; Agarwal, D. D.; J. Mo. Catal., 1988, 4, 65; Battioni, P.; Renaud, J. P.; Batioli, J. F.; Reina-Artiles, M; Fort, M.; Mansuy, D.; J. Am. Chem. Soc. 1988, 110, 8462.
  • Anderson , R. J. 1970 . J. Am. Chem. Soc. , 92 : 4978 (b) Gevorkyan, A. A; Kazaryan, P. I.; Avakyan, S. P.; Khim. Geterotsikl. Soedin., 1985, 450.
  • Chloroacetaldehyde is available from Aldrich Chemical Company as a 50% aqueous solution. (The pure material is unstable . The Merck Index , 10 ( 2075 )
  • Fujisawa , T. , Sato , T. , Kawar , T. and Ohashi , K. 1981 . Tetrahedron Lett. , : 4823
  • Gevorkyan , A. A. , Kazaryan , P. I. and Avakyan , S. V. 1988 . Zh. Org. Khim. , 24 : 1340
  • Kobayashi , Y. , Sato , F. , Suzuki , S. and Fujita , Y. Jpn. Kokai Tokkyo Koho, JP , 6226 279 Chem. Abs., 198?, 107, P154224r.
  • Trost , B. M. and Melvin , L. S. , eds. 1975 . Sulfur Ylides; Emerging Chemical Intermediates , N. Y : Academic Press . See, (b) Franzen, V., Driesen, H-E., Chem. Ber., 1963, 96, 1881; (c) Corey, E. J., Chaykovsky, M.;.J. Amer. Chem. Soc., 1965, 87, 1353;
  • Mosset , P. and Grée , R. 1985 . Synth. Commun. , 15 : 749
  • Physical and spectrosocopic data for (5): colourless liquid, b.p 105–175°C; vmax (neat) 3090 cm−1; δH (300 MHz, CDCl3) 1.15 (s, ca. 2H), 1.24 (s, ca. 1H), 1.57 (bs, 3H), 1.67 (A part of ABX multiplet, J 13Hz, J' 6.5Hz, J″ 6.5Hz, 1H), 1.80 (B part of ABX multiplet, J 13Hz, J' 6.5Hz, J″ 6.5Hz, 1H)1.98 (bt, J 6.5Hz, 2H), 2.70–2.81 (m, 2H), 2.96–3.03 (m, 1H), 6.09, 6.10 (2 × bs, superimposed, 1H); m/z (C. I., NH3) 172 (MNH4 +, 10%), 155 (MH+, 100%)
  • Keshel , G. N. and Farberov , M. I. 1964 . Izv. Vysshikh Uchebn. Zavadenii, Khim. i Khim. Tekhnol. , 7 : 639 Chem. Abs., 1965, 62, 3997e.

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