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
  • [1] REDUCTIVE DICARBONYL COUPLING WITH LOW-VALENT TITANIUM REAGENTS - A NEW ENTRY TO PHENANTHRENE ALKALOIDS
    SEIJAS, JA
    DELERA, AR
    VILLAVERDE, MC
    CASTEDO, L
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (12) : 839 - 840
  • [2] Reductive Umpolung Reactions with Low-Valent Titanium Catalysts
    Streuff, Jan
    CHEMICAL RECORD, 2014, 14 (06): : 1100 - 1113
  • [3] LOW-VALENT TITANIUM INDUCED REDUCTIVE CYCLIZATION OF NITROKETONE
    JIANG, JP
    GAO, J
    SHEN, WB
    CHEN, WX
    ACTA CHIMICA SINICA, 1992, 50 (11) : 1134 - 1139
  • [4] Low-valent titanium induced reductive deprotection of oximes
    Fan, XS
    Zhang, XY
    Zhang, YM
    JOURNAL OF CHEMICAL RESEARCH, 2004, (04) : 290 - 291
  • [5] A novel reductive cyclization of arylmethylidenemalononitrile promoted by low-valent titanium
    Shi, DQ
    Hong, Z
    Wang, XS
    Yao, CS
    Zhou, LH
    SYNTHETIC COMMUNICATIONS, 2002, 32 (21) : 3311 - 3317
  • [6] LOW-VALENT TITANIUM INDUCED REDUCTIVE REACTION OF THIOCYANATES AND ISOCYANATE
    Jian Xie CHEN
    ChineseChemicalLetters, 1993, (11) : 943 - 946
  • [7] REDUCTIVE ELIMINATION PATHWAYS TO LOW-VALENT TITANIUM ARYLOXIDE COMPLEXES
    DURFEE, LD
    FANWICK, PE
    ROTHWELL, IP
    FOLTING, K
    HUFFMAN, JC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4720 - 4722
  • [8] FACILE REDUCTIVE CLEAVAGE OF OXIMES WITH A LOW-VALENT TITANIUM REAGENT
    BALICKI, R
    KACZMAREK, L
    MALINOWSKI, M
    LIEBIGS ANNALEN DER CHEMIE, 1989, (11): : 1139 - 1140
  • [9] REDUCTIVE COUPLING OF AROMATIC KETONES BY LOW-VALENT TITANIUM SALTS
    BOTTINO, FA
    FINOCCHIARO, P
    LIBERTINI, E
    REALE, A
    RECCA, A
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1982, (01): : 77 - 81
  • [10] Low-valent titanium reductive coupling reactions of pyrrylaldehydes and pyrrylketones
    Cheng, JM
    Gano, JE
    Morgan, AR
    TETRAHEDRON LETTERS, 1996, 37 (16) : 2721 - 2724