A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions

被引:76
作者
Byrne, Peter A. [1 ]
Rajendran, Kamalraj V. [1 ]
Muldoon, Jimmy [1 ]
Gilheany, Declan G. [1 ]
机构
[1] Univ Coll Dublin, Sch Chem & Chem Biol, Ctr Synth & Chem Biol, Dublin 4, Ireland
基金
爱尔兰科学基金会;
关键词
PHOSPHINE OXIDES; PHOSPHONIUM SALTS; SOLID-STATE; REDUCTION; REAGENT; STEREOSELECTIVITY; TRIPHENYLPHOSPHINE; STEREOCHEMISTRY; TRANSFORMATION; MECHANISM;
D O I
10.1039/c2ob07074j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild method for the facile removal of phosphine oxide from the crude products of Wittig and Appel reactions is described. Work-up with oxalyl chloride to generate insoluble chlorophosphonium salt (CPS) yields phosphorus-free products for a wide variety of these reactions. The CPS product can be further converted into phosphine.
引用
收藏
页码:3531 / 3537
页数:7
相关论文
共 58 条
  • [1] Abell A. D., 2004, MODERN CARBONYL OLEF, pch 1
  • [2] Abell A.D., 2004, Organophosphorus Reagents, P99
  • [3] IONIC MOLECULAR ISOMERISM IN CHLOROPHENYLPHOSPHORANES PHNPCL5-N (1 LESS-THAN-OR-EQUAL-TO N LESS-THAN-OR-EQUAL-TO 3)
    ALJUBOORI, MAHA
    GATES, PN
    MUIR, AS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) : 1270 - 1271
  • [4] TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE
    APPEL, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12): : 801 - 811
  • [5] Appel R., 1979, Organophosphorus Reagents in Organic Synthesis, P387
  • [6] Synthesis of P-stereogenic phosphorus compounds. Asymmetric oxidation of phosphines under appel conditions
    Bergin, Enda
    O'Connor, Cormac T.
    Robinson, Shane B.
    McGarrigle, Eoghan M.
    O'Mahony, Colm P.
    Gilheany, Declan G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) : 9566 - +
  • [7] Improving the Atom Efficiency of the Wittig Reaction by a "Waste as Catalyst/Co-catalyst" Strategy
    Cao, Jun-Jie
    Zhou, Feng
    Zhou, Jian
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) : 4976 - 4980
  • [8] Key green chemistry research areas - a perspective from pharmaceutical manufacturers
    Constable, David J. C.
    Dunn, Peter J.
    Hayler, John D.
    Humphrey, Guy R.
    Leazer, Johnnie L., Jr.
    Linderman, Russell J.
    Lorenz, Kurt
    Manley, Julie
    Pearlman, Bruce A.
    Wells, Andrew
    Zaks, Aleksey
    Zhang, Tony Y.
    [J]. GREEN CHEMISTRY, 2007, 9 (05) : 411 - 420
  • [9] Development and application of a direct vinyl lithiation of cis-stilbene and a directed vinyl lithiation of an unsymmetrical cis-stilbene
    Cotter, Juliet
    Hogan, Anne-Marie L.
    O'Shea, Donal F.
    [J]. ORGANIC LETTERS, 2007, 9 (08) : 1493 - 1496
  • [10] Separation-friendly Mitsunobu reactions: A microcosm of recent developments in separation strategies
    Dandapani, S
    Curran, DP
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) : 3130 - 3138