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Volumn 46, Issue 1, 1998, Pages 187-189

Reduction of dithioacetals with SmI2 in benzene-HMPA

Author keywords

Dithioacetals; Reduction; Samarium iodide; Sulfides

Indexed keywords

ACETAL DERIVATIVE; BENZENE; HEMPA; SAMARIUM;

EID: 0031909081     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.187     Document Type: Article
Times cited : (8)

References (28)
  • 3
    • 33847086035 scopus 로고
    • Girard P., Namy J. L., Kagan H. B., J. Am. Chem. Soc., 102, 2693-2698 (1980); Handa Y., Inanaga J., Yamaguchi M., J. Chem. Soc., Chem. Commun., 1989, 298-299.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2693-2698
    • Girard, P.1    Namy, J.L.2    Kagan, H.B.3
  • 5
    • 33845374613 scopus 로고
    • Molander G. A., Hahn G., J. Org. Chem., 51, 1135-1138 (1986); Arai Y., Matsui M., Koizumi T., J. Chem. Soc., Perkin Trans. 1, 1990, 1233-1234.
    • (1986) J. Org. Chem. , vol.51 , pp. 1135-1138
    • Molander, G.A.1    Hahn, G.2
  • 7
    • 0025650399 scopus 로고    scopus 로고
    • Kende A. S., Mendoza J. S., Tetrahedron Lett., 31, 7105-7108 (1990); Künzer H., Stahnke M., Sauer G., Wiechert R., Tetrahedron Lett., 32, 1949-1952 (1991); Trost B. M., Neilsen J. B., Hoogsteen K., J. Am. Chem. Soc., 114, 5432-5434 (1992); Pouilly P., Chénedé A., Mallet J.-M., Sinaÿ P., Tetrahedron Lett., 33, 8065-8068 (1992); Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., Fukumoto K., Synlett, 1994, 859-860; Urban D., Skrydstrup T., Riche C., Chiaroni A., Beau J.-M., Chem. Commun., 1996, 1883-1884.
    • (1990) , vol.31 , pp. 7105-7108
    • Kende, A.S.1    Mendoza, J.S.2    Lett, T.3
  • 8
    • 0025907419 scopus 로고
    • Kende A. S., Mendoza J. S., Tetrahedron Lett., 31, 7105-7108 (1990); Künzer H., Stahnke M., Sauer G., Wiechert R., Tetrahedron Lett., 32, 1949-1952 (1991); Trost B. M., Neilsen J. B., Hoogsteen K., J. Am. Chem. Soc., 114, 5432-5434 (1992); Pouilly P., Chénedé A., Mallet J.-M., Sinaÿ P., Tetrahedron Lett., 33, 8065-8068 (1992); Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., Fukumoto K., Synlett, 1994, 859-860; Urban D., Skrydstrup T., Riche C., Chiaroni A., Beau J.-M., Chem. Commun., 1996, 1883-1884.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1949-1952
    • Künzer, H.1    Stahnke, M.2    Sauer, G.3    Wiechert, R.4
  • 9
    • 0009619238 scopus 로고
    • Kende A. S., Mendoza J. S., Tetrahedron Lett., 31, 7105-7108 (1990); Künzer H., Stahnke M., Sauer G., Wiechert R., Tetrahedron Lett., 32, 1949-1952 (1991); Trost B. M., Neilsen J. B., Hoogsteen K., J. Am. Chem. Soc., 114, 5432-5434 (1992); Pouilly P., Chénedé A., Mallet J.-M., Sinaÿ P., Tetrahedron Lett., 33, 8065-8068 (1992); Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., Fukumoto K., Synlett, 1994, 859-860; Urban D., Skrydstrup T., Riche C., Chiaroni A., Beau J.-M., Chem. Commun., 1996, 1883-1884.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5432-5434
    • Trost, B.M.1    Neilsen, J.B.2    Hoogsteen, K.3
  • 10
    • 0027094158 scopus 로고
    • Kende A. S., Mendoza J. S., Tetrahedron Lett., 31, 7105-7108 (1990); Künzer H., Stahnke M., Sauer G., Wiechert R., Tetrahedron Lett., 32, 1949-1952 (1991); Trost B. M., Neilsen J. B., Hoogsteen K., J. Am. Chem. Soc., 114, 5432-5434 (1992); Pouilly P., Chénedé A., Mallet J.-M., Sinaÿ P., Tetrahedron Lett., 33, 8065-8068 (1992); Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., Fukumoto K., Synlett, 1994, 859-860; Urban D., Skrydstrup T., Riche C., Chiaroni A., Beau J.-M., Chem. Commun., 1996, 1883-1884.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8065-8068
    • Pouilly, P.1    Chénedé, A.2    Mallet, J.-M.3    Sinaÿ, P.4
  • 11
    • 4344650647 scopus 로고    scopus 로고
    • Kende A. S., Mendoza J. S., Tetrahedron Lett., 31, 7105-7108 (1990); Künzer H., Stahnke M., Sauer G., Wiechert R., Tetrahedron Lett., 32, 1949-1952 (1991); Trost B. M., Neilsen J. B., Hoogsteen K., J. Am. Chem. Soc., 114, 5432-5434 (1992); Pouilly P., Chénedé A., Mallet J.-M., Sinaÿ P., Tetrahedron Lett., 33, 8065-8068 (1992); Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., Fukumoto K., Synlett, 1994, 859-860; Urban D., Skrydstrup T., Riche C., Chiaroni A., Beau J.-M., Chem. Commun., 1996, 1883-1884.
    • Synlett , vol.1994 , pp. 859-860
    • Ihara, M.1    Suzuki, S.2    Taniguchi, T.3    Tokunaga, Y.4    Fukumoto, K.5
  • 12
    • 0025650399 scopus 로고    scopus 로고
    • Kende A. S., Mendoza J. S., Tetrahedron Lett., 31, 7105-7108 (1990); Künzer H., Stahnke M., Sauer G., Wiechert R., Tetrahedron Lett., 32, 1949-1952 (1991); Trost B. M., Neilsen J. B., Hoogsteen K., J. Am. Chem. Soc., 114, 5432-5434 (1992); Pouilly P., Chénedé A., Mallet J.-M., Sinaÿ P., Tetrahedron Lett., 33, 8065-8068 (1992); Ihara M., Suzuki S., Taniguchi T., Tokunaga Y., Fukumoto K., Synlett, 1994, 859-860; Urban D., Skrydstrup T., Riche C., Chiaroni A., Beau J.-M., Chem. Commun., 1996, 1883-1884.
    • Chem. Commun. , vol.1996 , pp. 1883-1884
    • Urban, D.1    Skrydstrup, T.2    Riche, C.3    Chiaroni, A.4    Beau, J.-M.5
  • 14
    • 85045503520 scopus 로고    scopus 로고
    • Liu Y.-S., Bei M.-Z., Zhou Z.-H., Takai K., Fujiwara Y., Chem. Lett., 1992, 1143-1144; Park H. S., Lee I. S., Kim Y. H., Chem. Commun., 1996, 1805-1806.
    • Chem. Commun. , vol.1996 , pp. 1805-1806
    • Park, H.S.1    Lee, I.S.2    Kim, Y.H.3
  • 16
    • 0344052426 scopus 로고    scopus 로고
    • CAUTION: Since both benzene and HMPA are potent carcinogens, care should be taken in their use
    • CAUTION: Since both benzene and HMPA are potent carcinogens, care should be taken in their use.
  • 17
    • 0007182896 scopus 로고    scopus 로고
    • 2 in the benzene-HMPA system, see: Kunishima M., Hioki K., Ohara T., Tani S., J. Chem. Soc., Chem. Commun., 1992, 219-220; Kunishima M., Hioki K., Kato A., Tani S., Tetrahedron Lett., 35, 7253-7254 (1994); Kunishima M., Hioki K., Kono K., Sakuma T., Tani S., Chem. Pharm. Bull., 42, 2190-2192 (1994); Kunishima M., Hioki K., Kono K., Kato A., Tani S., J. Org. Chem., 62, 7542-7543 (1997); Ref. 1a).
    • J. Chem. Soc., Chem. Commun. , vol.1992 , pp. 219-220
    • Kunishima, M.1    Hioki, K.2    Ohara, T.3    Tani, S.4
  • 18
    • 0028100610 scopus 로고
    • 2 in the benzene-HMPA system, see: Kunishima M., Hioki K., Ohara T., Tani S., J. Chem. Soc., Chem. Commun., 1992, 219-220; Kunishima M., Hioki K., Kato A., Tani S., Tetrahedron Lett., 35, 7253-7254 (1994); Kunishima M., Hioki K., Kono K., Sakuma T., Tani S., Chem. Pharm. Bull., 42, 2190-2192 (1994); Kunishima M., Hioki K., Kono K., Kato A., Tani S., J. Org. Chem., 62, 7542-7543 (1997); Ref. 1a).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7253-7254
    • Kunishima, M.1    Hioki, K.2    Kato, A.3    Tani, S.4
  • 19
    • 0028061479 scopus 로고
    • 2 in the benzene-HMPA system, see: Kunishima M., Hioki K., Ohara T., Tani S., J. Chem. Soc., Chem. Commun., 1992, 219-220; Kunishima M., Hioki K., Kato A., Tani S., Tetrahedron Lett., 35, 7253-7254 (1994); Kunishima M., Hioki K., Kono K., Sakuma T., Tani S., Chem. Pharm. Bull., 42, 2190-2192 (1994); Kunishima M., Hioki K., Kono K., Kato A., Tani S., J. Org. Chem., 62, 7542-7543 (1997); Ref. 1a).
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 2190-2192
    • Kunishima, M.1    Hioki, K.2    Kono, K.3    Sakuma, T.4    Tani, S.5
  • 20
    • 0000095069 scopus 로고    scopus 로고
    • Ref. 1a
    • 2 in the benzene-HMPA system, see: Kunishima M., Hioki K., Ohara T., Tani S., J. Chem. Soc., Chem. Commun., 1992, 219-220; Kunishima M., Hioki K., Kato A., Tani S., Tetrahedron Lett., 35, 7253-7254 (1994); Kunishima M., Hioki K., Kono K., Sakuma T., Tani S., Chem. Pharm. Bull., 42, 2190-2192 (1994); Kunishima M., Hioki K., Kono K., Kato A., Tani S., J. Org. Chem., 62, 7542-7543 (1997); Ref. 1a).
    • (1997) J. Org. Chem. , vol.62 , pp. 7542-7543
    • Kunishima, M.1    Hioki, K.2    Kono, K.3    Kato, A.4    Tani, S.5
  • 21
    • 0345346132 scopus 로고    scopus 로고
    • note
    • 2 gradually decomposed during a long period of reaction probably due to contamination with air.
  • 22
    • 0344914913 scopus 로고    scopus 로고
    • note
    • 2 under similar reaction conditions, the low yields of 2d can be attributed to further reduction.
  • 23
    • 0344052421 scopus 로고    scopus 로고
    • Determined by proton NMR
    • Determined by proton NMR.
  • 25
    • 0025868967 scopus 로고    scopus 로고
    • For conversion of dithioacetals into sulfides, see: Krief A., Kenda B., Barbeaux P., Tetrahedron Lett., 32, 2509-2512 (1991); Ikehira H., Tanimoto S., Oida T., J. Chem. Soc., Perkin Trans. 1, 1984, 1223-1226; Kikugawa Y., J. Chem. Soc., Perkin Trans. 1, 1984, 609-610; Cohen T., Daniewski W. M., Weisenfeld R. B., Tetrahedron Lett., 1978, 4665-4668.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2509-2512
    • Krief, A.1    Kenda, B.2    Barbeaux, P.3
  • 26
    • 37049106507 scopus 로고    scopus 로고
    • For conversion of dithioacetals into sulfides, see: Krief A., Kenda B., Barbeaux P., Tetrahedron Lett., 32, 2509-2512 (1991); Ikehira H., Tanimoto S., Oida T., J. Chem. Soc., Perkin Trans. 1, 1984, 1223-1226; Kikugawa Y., J. Chem. Soc., Perkin Trans. 1, 1984, 609-610; Cohen T., Daniewski W. M., Weisenfeld R. B., Tetrahedron Lett., 1978, 4665-4668.
    • J. Chem. Soc., Perkin Trans. 1 , vol.1984 , pp. 1223-1226
    • Ikehira, H.1    Tanimoto, S.2    Oida, T.3
  • 27
    • 0025868967 scopus 로고    scopus 로고
    • For conversion of dithioacetals into sulfides, see: Krief A., Kenda B., Barbeaux P., Tetrahedron Lett., 32, 2509-2512 (1991); Ikehira H., Tanimoto S., Oida T., J. Chem. Soc., Perkin Trans. 1, 1984, 1223-1226; Kikugawa Y., J. Chem. Soc., Perkin Trans. 1, 1984, 609-610; Cohen T., Daniewski W. M., Weisenfeld R. B., Tetrahedron Lett., 1978, 4665-4668.
    • J. Chem. Soc., Perkin Trans. 1 , vol.1984 , pp. 609-610
    • Kikugawa, Y.1
  • 28
    • 0025868967 scopus 로고    scopus 로고
    • For conversion of dithioacetals into sulfides, see: Krief A., Kenda B., Barbeaux P., Tetrahedron Lett., 32, 2509-2512 (1991); Ikehira H., Tanimoto S., Oida T., J. Chem. Soc., Perkin Trans. 1, 1984, 1223-1226; Kikugawa Y., J. Chem. Soc., Perkin Trans. 1, 1984, 609-610; Cohen T., Daniewski W. M., Weisenfeld R. B., Tetrahedron Lett., 1978, 4665-4668.
    • Tetrahedron Lett. , vol.1978 , pp. 4665-4668
    • Cohen, T.1    Daniewski, W.M.2    Weisenfeld, R.B.3


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