α-Phosphoryl sulfoxides. XI. Sulfenylation of α-phosphoryl sulfoxides and a general synthesis of optically active ketene dithioacetal mono-S-oxides

Tetrahedron

Volumn 53, Issue 8, 1997, Pages 2959-2972

  Mikołajczyk, Marian ^a   Midura, Wanda H ^a   Wladislaw, Blanka ^b   Biaggio, Francisco C ^b   Marzorati, Liliana ^b   Wieczorek, Michał W ^c   Błaszczyk, Jarosław ^c  

^a POLISH ACADEMY OF SCIENCES   (Poland)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584873     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01175-1     Document Type: Article

References (38)

1. 1. For part X on α-phosphoryl sulfoxides see: Mikołajczyk, M., Krysiak, J.A., Midura, W.H., Wieczorek, M.W., Błaszczyk, J. Tetrahedron: Asymmetry, in press.
2. 2. This paper belongs to a Brazilian series of papers on sulfenylation of organic compounds; for a previous paper see: Wladislaw, B., Marzorati, L., Di Vitta, C. and Claro, N.F. Junior, Synth. Comm., 1996, 26, 3485.
3. 3. The main part of the results reported here was presented at the XIIIth International Conference on Phosphorus Chemistry, Jerusalem, 1995 (Abstract Book, p. 177).
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12. 12. For a successful use of this reagent in the sulfenylation reactions of various organic sulfur compounds see: Wladislaw, B., Marzorati, L. Rev. Heteroatom Chem., Ed. Oae, S., Myu, Tokyo, 1993, 9, 49-60. See also: Wladislaw, B., Marzorati, L. and Biaggio, F.C. J. Org. Chem., 1993, 58, 6132; Wladislaw, B., Marzorati, L. and Donnici, C.L. J. Chem. Soc. Perkin Trans I, 1993, 3167; Wladislaw, B., Marzorati, L., and Zaim, M.H. Phosphorus Sulfur and Silicon, 1994, 92, 11.
13. 12. For a successful use of this reagent in the sulfenylation reactions of various organic sulfur compounds see: Wladislaw, B., Marzorati, L. Rev. Heteroatom Chem., Ed. Oae, S., Myu, Tokyo, 1993, 9, 49-60. See also: Wladislaw, B., Marzorati, L. and Biaggio, F.C. J. Org. Chem., 1993, 58, 6132; Wladislaw, B., Marzorati, L. and Donnici, C.L. J. Chem. Soc. Perkin Trans I, 1993, 3167; Wladislaw, B., Marzorati, L., and Zaim, M.H. Phosphorus Sulfur and Silicon, 1994, 92, 11.
14. 12. For a successful use of this reagent in the sulfenylation reactions of various organic sulfur compounds see: Wladislaw, B., Marzorati, L. Rev. Heteroatom Chem., Ed. Oae, S., Myu, Tokyo, 1993, 9, 49-60. See also: Wladislaw, B., Marzorati, L. and Biaggio, F.C. J. Org. Chem., 1993, 58, 6132; Wladislaw, B., Marzorati, L. and Donnici, C.L. J. Chem. Soc. Perkin Trans I, 1993, 3167; Wladislaw, B., Marzorati, L., and Zaim, M.H. Phosphorus Sulfur and Silicon, 1994, 92, 11.
15. 12. For a successful use of this reagent in the sulfenylation reactions of various organic sulfur compounds see: Wladislaw, B., Marzorati, L. Rev. Heteroatom Chem., Ed. Oae, S., Myu, Tokyo, 1993, 9, 49-60. See also: Wladislaw, B., Marzorati, L. and Biaggio, F.C. J. Org. Chem., 1993, 58, 6132; Wladislaw, B., Marzorati, L. and Donnici, C.L. J. Chem. Soc. Perkin Trans I, 1993, 3167; Wladislaw, B., Marzorati, L., and Zaim, M.H. Phosphorus Sulfur and Silicon, 1994, 92, 11.
16. 13. In the case of sulfenylation of α-phosphorylmethyl methyl sulfoxide 8d the reaction does not have synthetic value since the mixture of different products including α-phosphoryldithioacetal is obtained. Moreover, during purification by chromatography unstable products undergo decomposition affording among others S-methyl α-phosphorylthioformate
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