Reduction of dithioacetals with SmI2 in benzene-HMPA

Chemical and Pharmaceutical Bulletin

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

  Kunishima, Munetaka ^a   Nakata, Daisuke ^a   Hioki, Kazuhito ^a   Tani, Shohei ^a  

^a KOBE GAKUIN UNIVERSITY   (Japan)

Author keywords

Dithioacetals; Reduction; Samarium iodide; Sulfides

Indexed keywords

ACETAL DERIVATIVE; BENZENE; HEMPA; SAMARIUM;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION;

EID: 0031909081     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.187     Document Type: Article

References (28)

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10. 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.
11. 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.
12. 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.
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16. CAUTION: Since both benzene and HMPA are potent carcinogens, care should be taken in their use.
17. 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).
18. 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).
19. 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).
20. 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).
21. 2 gradually decomposed during a long period of reaction probably due to contamination with air.
22. 2 under similar reaction conditions, the low yields of 2d can be attributed to further reduction.
23. Determined by proton NMR.
24. Greene T. W., Wuts P. G. M., "Protective Groups in Organic Synthesis," 2nd ed., John Wiley & Sons, Inc., New York, 1991, pp. 198-207.
25. 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.
26. 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.
27. 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.
28. 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.