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Volumn 2, Issue 2, 2005, Pages 198-200

A mild and efficient synthesis of disecondary phosphines using CsOH: Efforts toward phosphine macrocycles

Author keywords

Cesium hydroxide monohydrate; Dialkyl halide; Disecondary phosphine; Phosphine macrocycle; Primary phosphine

Indexed keywords


EID: 27944468173     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053202874     Document Type: Review
Times cited : (4)

References (29)
  • 20
    • 46149119079 scopus 로고
    • When the chain length between the dihalide is less than three carbons long, the reaction can lead to the formation of phosphirans, see: a, Barton, D, Ollis, W.D, Eds, Pergamon Press: UK
    • When the chain length between the dihalide is less than three carbons long, the reaction can lead to the formation of phosphirans, see: (a) Smith, D.J.H. In Comprehensive Organic Synthesis; Barton, D.; Ollis, W.D., Eds.; Pergamon Press: UK, 1979, Vol. 2, pp. 1138-1139.
    • (1979) Comprehensive Organic Synthesis , vol.2 , pp. 1138-1139
    • Smith, D.J.H.1
  • 21
    • 84981835462 scopus 로고
    • For generation of phosphide anions, see: b
    • For generation of phosphide anions, see: (b) Issleib, K.; Weichmann, H. Chem. Ber. 1968, 101, 2197.
    • (1968) Chem. Ber , vol.101 , pp. 2197
    • Issleib, K.1    Weichmann, H.2
  • 26
    • 1442310908 scopus 로고    scopus 로고
    • Phosphorus, Sulfur, and Silicon, and Relat. Elem
    • Honaker, M.T.; Salvatore, R.N. Phosphorus, Sulfur, and Silicon, and Relat. Elem. 2004, 2, 277.
    • (2004) , vol.2 , pp. 277
    • Honaker, M.T.1    Salvatore, R.N.2
  • 27
    • 46149094539 scopus 로고    scopus 로고
    • Molecular sieves accelerated the alkylation by removal of water from the reaction media, at °C prior to use, reactions were sluggish resulting in diminished product yields with recovery of the starting phosphine predominately
    • Molecular sieves accelerated the alkylation by removal of water from the reaction media. When molecular sieves were not activated by drying for 24 b at 120 °C prior to use, reactions were sluggish resulting in diminished product yields with recovery of the starting phosphine predominately.
    • When molecular sieves were not activated by drying for 24 b , pp. 120
  • 28
    • 46149097536 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Disecondary Phosphines, 3a-f, Representative procedure for 1,2-bis(phenylphosphino) ethane, 3b, To a suspension containing activated powdered 4 Å molecular sieves (2 g) in anhydrous N,N-dimethylformamide (18.2 mL) cesium hydroxide monohydrate (1.22 g, 7.28 mmol) was added and the mixture was stirred under a dry nitrogen atmosphere. After phenylphosphine (0.4 mL, 3.36 mmol, 1) was added, the reaction mixture was stirred for 1 hour resulting in a deep colored yellow solution. 1,2-Dibromoethane (0.16 mL, 1.82 mmol, 2b) was added in one portion, at which point, the mixture turned immediately to milky white. The reaction was allowed to proceed at room temperature for 45 h, at which point, 1 was consumed (TLC, Degassed water (30 mL) was added and the mixture was subsequently extracted with CH2Cl2 3 × 30 mL, The combined organic layers were then washed with degassed wate
    • 2: C, 68.29; H, 6.55; P, 25.16. Found: C, 68.32; H, 6.50.
  • 29
    • 3242663729 scopus 로고    scopus 로고
    • Recently, a general method for the sequestering of CuCl and the reclaiming of mono- and bidentate phosphines was reported, see
    • Recently, a general method for the sequestering of CuCl and the reclaiming of mono- and bidentate phosphines was reported, see: Lipshutz, B.H.; Frieman, B.; Birkedal, H. Org. Lett. 2004, 6, 2305.
    • (2004) Org. Lett , vol.6 , pp. 2305
    • Lipshutz, B.H.1    Frieman, B.2    Birkedal, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.