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Letters in Organic Chemistry
Volumn 4, Issue 2, 2007, Pages 109-111
Base catalyzed double addition of secondary phosphine chalcogenides to benzoylacetylene
Author keywords

and ; addition; Benzoylacetylene; Nucleophilic ; Secondary phosphine oxides; Secondary phosphine sulfides
Indexed keywords

EID: 34247853468     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807780414109     Document Type: Article
Times cited : (22)
References (34)
  • 11
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    • Jacobsen, E.N, Pfaltz, A, Yamamoto, H, Eds, Springer: Berlin
    • (b) Comprehensive Asymmetric Catalysis; Jacobsen, E.N.; Pfaltz, A.; Yamamoto, H.; Eds.; Springer: Berlin, 1999;
    • (1999) Comprehensive Asymmetric Catalysis
  • 12
    • 0003544583 scopus 로고    scopus 로고
    • Ojima, I, Ed, 2nd ed, VCH Publishers: Weinheim
    • (c) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; 2nd ed.; VCH Publishers: Weinheim, 2000;
    • (2000) Catalytic Asymmetric Synthesis
  • 23
    • 34247845725 scopus 로고    scopus 로고
    • Trofimov, B.A.; Arbuzova, S.N.; Gusarova, N.K. Usp. Khim., 1999, 68, 240 Russ. Chem. Rev., 1999, 68, 215 (Engl Transl).
    • (c) Trofimov, B.A.; Arbuzova, S.N.; Gusarova, N.K. Usp. Khim., 1999, 68, 240 Russ. Chem. Rev., 1999, 68, 215 (Engl Transl).
  • 25
    • 33846917737 scopus 로고    scopus 로고
    • Dvorko, M. Yu.; Albanov, A.I.; Chipanina, N.N., Sherstyannikova, L.V.; Samoilov, V.G.; Komarova, T.N.; Glotova, T.E. Khim. Geterotsikl. Soed, 2006, 1655 Chem. Heterocycl. Compd., 2006, 42, 142 1 (Engl. Transl).
    • Dvorko, M. Yu.; Albanov, A.I.; Chipanina, N.N., Sherstyannikova, L.V.; Samoilov, V.G.; Komarova, T.N.; Glotova, T.E. Khim. Geterotsikl. Soed, 2006, 1655 Chem. Heterocycl. Compd., 2006, 42, 142 1 (Engl. Transl).
  • 26
    • 34247883956 scopus 로고    scopus 로고
    • General procedure for the synthesis of 3: A suspension of benzoylacetylene 1 (0.50 mmol, bis(2-phenethyl)phosphine chalcogenide 2 (1.00 mmol) and KOH·0.5H2O (15% water content, 0.17 mmol) in 4 mL, of THF was stirred at 63-65 °C for 18 h (in the case of 2a) or at rt for 2 h (in the case of 2b, The reaction mixture was passed through a layer of calcined Al2O3 (0.5 cm, the latter was additionally washed with 7 mL of THF, and THF was distilled off under reduced pressure. 3,3-Bis(diphenethylphosphoryl)-1-phenyl-1-propanone 3a. The crude product (light-yellow oil) was washed with an ether: petroleum ether (a fraction with bp of 40-60 °C) mixture (1: 2, 4 × 1 mL) and dried under vacuum to give the compound 3a in 38% yield. Colorless waxy product; IR (KBr, cm-1, 1675 (C=O, 1160 (P=O, 1H NMR (400.13 MHz, CDCl3, δ 1.98-2.44 m, 8H, CH2P
    • 2 (678.87): C, 72.54; H, 6.53; P, 9.13, S, 9.45. Found: C, 72.76; H, 6.42; P, 8.98; S, 9.24.
  • 29
    • 34247883955 scopus 로고    scopus 로고
    • Experimental procedure: A suspension of benzoylacetylene 1 (0.50 mmol, diphenylphosphine oxide 4 (1.00 mmol) and KOH-0.5H2O (15% water content, 0.17 mmol) in 6 mL of THF was stirred at rt for 2 h. The precipitate formed was filtered off and dissolved in 4 mL of chloroform. The chloroform solution was washed with water (2 × 5 mL, dried over Na2SO4 and filtered. Chloroform was distilled off from the extract under reduced pressure, the residue was dried under vacuum to give the compound 5. Trace amounts of the diadducts 5 and 6 were detected in the mother liquor (31 P NMR, 2,3-Bis(diphenylphosphoryl)-1-phenyl-1-propanone 5. Yield 67, white powder, mp 200-202 °C. IR (KBr, cm-1, 1670 (C=O, 1180 (P=O, 1H NMR (400.13 MHz, CDCl3, δ 2.78 dd, 1H, H-2′, 2J2′P 26.9 Hz, 2J2′2″
    • 2 (534.52): C, 74.15; H, 5.28; P, 11.59. Found: C, 74.38; H, 5.35; P, 11.40.
  • 32
    • 34247855452 scopus 로고    scopus 로고
    • Experimental procedure: To a suspension of benzoylacetylene 1 (0.50 mmol) and KOH·0.5H2O (15% water content, 0.17 mmol) in 3 mL of THF, diphenylphosphine oxide 4 (1.00 mmol) in 3 mL of THF was slowly added dropwise over 1 h 40 min. The reaction mixture was stirred at rt for 3 h and then for another 3 h upon heating (63-65 °C, then cooled. The solvent was distilled off under reduced pressure. The residue was dissolved in 4 mL of chloroform, the chloroform solution was washed with water (2 × 5 mL, dried over Na2SO4 and filtered. Chloroform was removed under reduced pressure to give an oil-like compound, which crystallized upon storage and, according to 1H NMR, consisted of a mixture of the diadduct 6 (major product) and diadduct 5 (trace amounts, After recrystallization from ether, the compound 6 was obtained. 3,3-Bis(diphenylphosphoryl)-1-phenyl-1-propanone 6. Yield 70, whi
    • 2 (534.52): C, 74.15; H, 5.28; P, 11.59. Found: C, 74.02; H, 5.24; P, 11.35.

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