Purification technique for the removal of ruthenium from olefin metathesis reaction products

被引:251
作者
Maynard, HD [1 ]
Grubbs, RH [1 ]
机构
[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synthesis, Pasadena, CA 91125 USA
关键词
D O I
10.1016/S0040-4039(99)00726-1
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Ring-closing metathesis (RCM) products of reactions utilizing RuCl2(=CHPh)(PCy3)(2) (1) as a catalyst were successfully purified of unwanted ruthenium using a water-soluble coordinating phosphine, tris(hydroxymethyl)phosphine, P(CH2OH)(3). Several simple and efficient purification procedures were compared for the isolation of the product of the RCM of diethyl diallylmalonate. The efficiency of this procedure was demonstrated for the isolation of crown-ether 3. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4137 / 4140
页数:4
相关论文
共 17 条
[1]
In vitro and in vivo characterization of a Tc-99m complex with tris(hydroxymethyl)phosphine (THP) [J].
Berning, DE ;
Katti, KV ;
Singh, PR ;
Higgenbotham, C ;
Reddy, VS ;
Volkert, WA .
NUCLEAR MEDICINE AND BIOLOGY, 1996, 23 (05) :617-622
[2]
Chemistry in environmentally benign media .8. Hydroxymethyl functionalized phosphanes as building blocks to new water-soluble gold(I) complexes - Synthesis, characterization, and X-ray crystal structures of novel tetrahedral [Au{P(CH2OH)(3)}(4)](+) and trigonal planar [Au(Ph2PCH2OH)(3)](+) gold(I) complexes [J].
Berning, DE ;
Katti, KV ;
Barnes, CL ;
Volkert, WA .
CHEMISCHE BERICHTE-RECUEIL, 1997, 130 (07) :907-911
[3]
Multifaceted reactions of P(CH2OH)3 with rhenium(V) precursors.: Synthesis, characterization, and X-ray structural studies of trans,trans,trans-[ReO2{P(CH2OH)3}2(py)2]Cl, trans,cis,cis-[ReO2{P(CH2OH)3}2(py)2]Cl, and novel alkoxide [Re(O)(μ-O)-(P{CH2OH}3)(μ-η2-P{CH2OH}2CH2O)]4 [J].
Berning, DE ;
Katti, KV ;
Barbour, LJ ;
Volkert, WA .
INORGANIC CHEMISTRY, 1998, 37 (02) :334-339
[4]
Selective two-phase-hydrogenation of sorbic acid with novel water soluble ruthenium complexes [J].
Driessen-Holscher, B ;
Heinen, J .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 570 (01) :141-146
[5]
WATER-SOLUBLE TRIS(HYDROXYMETHYL)PHOSPHINE COMPLEXES WITH NICKEL, PALLADIUM, AND PLATINUM - CRYSTAL-STRUCTURE OF [PD(P(CH2OH)3)4].CH3OH [J].
ELLIS, JW ;
HARRISON, KN ;
HOYE, PAT ;
ORPEN, AG ;
PRINGLE, PG ;
SMITH, MB .
INORGANIC CHEMISTRY, 1992, 31 (14) :3026-3033
[6]
Synthesis and reactivity of the ferrocene-derived phosphine [Fe(eta-C5H5)-{eta-C5H4CH2P(CH2OH)(2)}] [J].
Goodwin, NJ ;
Henderson, W ;
Nicholson, BK ;
Sarfo, JK ;
Fawcett, J ;
Russell, DR .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (22) :4377-4384
[7]
GRUBBS RH, 1998, J MOL CATAL A-CHEM, V133, P1
[8]
Formation and X-ray structure of a novel water-soluble tertiary-secondary phosphine complex of ruthenium(II):: [Ru{P(CH2OH)3}2{P(CH2OH)2H}2Cl2] [J].
Higham, L ;
Powell, AK ;
Whittlesey, MK ;
Wocadlo, S ;
Wood, PT .
CHEMICAL COMMUNICATIONS, 1998, (10) :1107-1108
[9]
HYDROPHOSPHINATION OF FORMALDEHYDE CATALYZED BY TRIS-(HYDROXYMETHYL)PHOSPHINE COMPLEXES OF PLATINUM, PALLADIUM OR NICKEL [J].
HOYE, PAT ;
PRINGLE, PG ;
SMITH, MB ;
WORBOYS, K .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (02) :269-274
[10]
Effects of olefin substitution on the ring-closing metathesis of dienes [J].
Kirkland, TA ;
Grubbs, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7310-7318