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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 9-10
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Original Articles

A New Tin(II) Chloride-Silver(I) Acetate or -Lead(II) Bromide Reagent for the Addition of F-Alkyl Iodides to Alkenes

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Pages 1611-1617 | Received 09 Sep 1988, Published online: 24 Oct 2006

References

  • Leedham , K. and Haszeldine , R. N. 1954 . J. Chem. Soc. , : 1634 Brace, N. O. and Van Elswyk, J. E., J. Org. Chem., 1976, 41, 766; Baum, K., Bedford, C. D., and Hunadi, R. J., ibid., 1982, 47, 2251.
  • Haszeldine , R. N. 1951 . J. Chem. Soc. , : 588 Haszeldine, R. N. and Steele, B. R., ibid., 1953, 1199.
  • Calas , P. and Commeyras , A. 1980 . J. Fluorine Chem. , 16 : 553 Calas, P., Moreau, P., and Commeyras, A., J. Chem. Soc., Chem. Commun., 1982, 433.
  • Fuchikami , T. and Ojima , I. 1984 . Tetrahedron Lett. , 25 : 303 Idem ibid., 1984, 25, 307; Werner, K. V., J. Fluorine Chem., 1985, 28, 229; Chen, Q. Y., He, Y. B., and Yang, Z. Y., ibid., 1986, 34, 255; Chen, Q. Y. and Yang, Z. Y., J. Chem. Soc., Chem. Commun., 1986, 498; Ishihara, T., Kuroboshi, M., and Okada, Y., Chem. Lett., 1986, 1895; Urata, H., Yugari, H., and Fuchikami, T., ibid., 1987, 833; Chen, Q. Y., Qiu, Z. M., and Yang, Z. Y., J. Fluorine Chem., 1987, 36, 149; Matsubara, S., Mitani, M., and Utimoto, K., Tetrahedron Lett., 1987, 28, 5857; Kuroboshi, M. and Ishihara, T., J. Fluorine Chem., 1988, 39, 299.
  • Kitazume , T. and Ikeya , T. 1987 . the 54th National Meeting of the Chemical Society of Japan, Tokyo, Japan, April, Abstr. No. 3 III037;Ikeya, T. and Kitazume, T., the 12th Symposium on Fluorine Chemistry, Hakata, Japan, October 1987, Abstr. No. 3R17; Kitazume, T. and Ikeya, T., J. Org. Chem., 1988, 53, 2350.
  • Uneyama , K. , Nanbu , H. and Torii , S. 1986 . Tetrahedron Lett. , 27 : 2395 The combined reagents of metals and/or metal salts have been used for the allylation of carbonyl compounds. See:;Wada, M., Ohki, H., and Akiba, K., ibid., 1986, 27, 4771; Tanaka, H., Yamashita, S., Ikemoto, Y., and Torii, S., Chem. Lett., 1987, 673, and references cited therein.
  • To a mixture of acid-washed tin powder8 (1 mmo1) and AgOAc (0.15 mmo1) in methanol (1.5 mL) were added RfI (1 mmo1) and allyl or homoallyl alcohol (1.5 mmo1) under argon. This mixture was stirred at room temperature for 20 h. A usual workup followed by column chromatography gave the addition product.
  • Commercially available tin powder was washed successively with dilute hydrochloric acid, methanol, and diethyl ether, and dried under vacuum.
  • Kitazume , T. and Ishikawa , N. 1981 . the 7th Symposium on Fluorine Chemistry, Okayama, Japan, October, Abstr. No. 3Z04.

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