REDUCTIVE PROPERTIES OF LOW-VALENT TITANIUM REAGENTS - MECHANISTIC STUDIES

被引:7
|
作者
MALINOWSKI, M [1 ]
KACZMAREK, L [1 ]
ROZPLOCH, F [1 ]
机构
[1] NICHOLAS COPERNICUS UNIV,INST PHYS,PL-87100 TORUN,POLAND
关键词
D O I
10.1039/p29910000879
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reduction of nitro compounds and the deoxygenation of N-oxides with low-valent titanium reagents were studied. The reaction conditions were optimized. Both the inorganic and the organic part of the reaction are discussed. The reaction mechanism is deduced from stoichiometric studies and EPR measurements. Formation of an intermediate complex of an organic anion-radical with titanium is proposed as the key step in the reduction of nitro compounds and the deoxygenation of N-oxides with low-valent titanium. In general, this mechanism is similar to that proposed earlier for the reductive coupling of ketones.
引用
收藏
页码:879 / 883
页数:5
相关论文
共 50 条
  • [31] LOW-VALENT TITANIUM INDUCED REDUCTIVE COUPLING OF NITRILES WITH NITRO-COMPOUNDS
    CHEN, JX
    CHAI, WY
    ZHU, JL
    GAO, J
    CHEN, WX
    KAO, TY
    SYNTHESIS-STUTTGART, 1993, (01): : 87 - 88
  • [32] LOW-VALENT TITANIUM INDUCED REDUCTIVE CYCLIZATION OF NITRILES TO SYMMETRICALLY SUBSTITUTED TETRAALKYLPYRAZINES
    CHEN, WX
    ZHANG, JH
    HU, MY
    WANG, XC
    SYNTHESIS-STUTTGART, 1990, (08): : 701 - 702
  • [33] Low-Valent Titanium Induced Reductive Elimination: Synthesis of Optically Active Trienols
    Solladie, Guy
    Hamdouchi, Chafiq
    SYNLETT, 1989, (01) : 66 - U97
  • [34] Reductive coupling reaction of aryliminomethylferrocenes with triethyl orthoformate induced by low-valent titanium
    Gong, JF
    Wu, YJ
    Cui, XL
    Du, CX
    Zhu, Y
    CHINESE JOURNAL OF CHEMISTRY, 2001, 19 (09) : 893 - 900
  • [35] Low-valent titanium induced novel reductive cyclizations of αβ-unsaturated nitrile compounds
    Zhou, LH
    Tu, SJ
    Shi, DQ
    Dai, GY
    Chen, WX
    SYNTHESIS-STUTTGART, 1998, (06): : 851 - 854
  • [36] Formation of carbenoid intermediates in the reaction of ditertiobutyl ketone with low-valent titanium reagents
    Villiers, C
    Vandais, A
    Ephritikhine, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) : 744 - 747
  • [37] STEREOCONTROLLED REDUCTIVE DEOXYGENATION USING LOW-VALENT TITANIUM - EFFECTS OF ULTRASOUND WAVES AND SOLVENTS
    NAYAK, SK
    BANERJI, A
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05): : 1940 - 1942
  • [38] LOW-VALENT TITANIUM INDUCED REDUCTIVE COUPLING REACTION OF CARBOXYLIC DERIVATIVES WITH AROMATIC KETONES
    SHI, DQ
    CHEN, JX
    CHAI, WY
    CHEN, WX
    KAO, TY
    TETRAHEDRON LETTERS, 1993, 34 (18) : 2963 - 2964
  • [39] SYNTHESIS OF NEW AROMATIC RETINOID ANALOGS BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION
    SOLLADIE, G
    GIRARDIN, A
    LANG, G
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11): : 2620 - 2628
  • [40] REDUCTIVE COUPLING OF BENZOIC-ACID HALIDES AND ESTERS USING LOW-VALENT TITANIUM
    DANG, Y
    GEISE, HJ
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1991, 100 (05): : 375 - 380