Oxidative nucleophilic substitution of hydrogen in nitro(pentafluorosulfanyl)benzenes with alkyl Grignard and lithium reagents

被引:26
|
作者
Vida, Norbert [1 ]
Beier, Petr [1 ]
机构
[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, CR-16610 Prague, Czech Republic
关键词
Pentafluorosulfanyl group; Nucleophilic aromatic substitutions; Oxidations; HYPERVALENT SULFUR FLUORIDES; NITROARENES; CONSTITUTION;
D O I
10.1016/j.jfluchem.2012.04.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Alkyl Grignard and lithium reagents underwent nucleophilic addition to para- and meta-nitro(pentafluorosulfanyl)benzenes in ether solvents to form sigma(H) adducts, which were oxidized with potassium permanganate in liquid ammonia to yield products of oxidative nucleophilic substitution of hydrogen in moderate to good yields. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码:130 / 134
页数:5
相关论文
共 50 条
  • [31] Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetic acid derivatives
    Makosza, M
    Kamienska-Trela, K
    Paszewski, M
    Bechcicka, M
    TETRAHEDRON, 2005, 61 (50) : 11952 - 11964
  • [32] Oxidative nucleophilic substitution of hydrogen in nitroarenes by silyl enol ethers
    Makosza, M
    Surowiec, M
    TETRAHEDRON, 2003, 59 (33) : 6261 - 6266
  • [33] Aromatic nucleophilic substitution in 1,2,4-triazine 4-oxides with Grignard reagents
    Prokhorov, AM
    Kozhevnikov, DN
    Rusinov, VL
    Chupakhin, ON
    POLISH JOURNAL OF CHEMISTRY, 2003, 77 (09) : 1157 - 1161
  • [34] PHOTOCHEMICAL REACTIONS OF HALO SUBSTITUTION BY HYDROGEN IN ARYL HALIDES BY ACTIVITY OF NUCLEOPHILIC REAGENTS
    KULIS, YY
    POLETAEV.IY
    KUZMIN, MG
    ZHURNAL ORGANICHESKOI KHIMII, 1973, 9 (06): : 1214 - 1218
  • [35] NUCLEOPHILIC AROMATIC-SUBSTITUTION OF 2-SULFONYL-SUBSTITUTED 1-METHOXYNAPHTHALENES WITH GRIGNARD-REAGENTS
    HATTORI, T
    SUZUKI, M
    KOMURO, Y
    MIYANO, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12): : 1473 - 1474
  • [36] Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding
    Champagne, Pier Alexandre
    Pomarole, Julien
    Therien, Marie-Eve
    Benhassine, Yasmine
    Beaulieu, Samuel
    Legault, Claude Y.
    Paquin, Jean-Francois
    ORGANIC LETTERS, 2013, 15 (09) : 2210 - 2213
  • [37] Synthesis of α-(Nitroaryl)benzylphosphonates via Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes
    Makosza, Mieczyslaw
    Sulikowski, Daniel
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3827 - 3832
  • [38] Hydroxylation of nitroarenes with alkyl hydroperoxide anions via Vicarious Nucleophilic Substitution of hydrogen
    Makosza, M
    Sienkiewicz, K
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13): : 4199 - 4208
  • [39] Oxidative nucleophilic substitution of hydrogen in nitrobenzenes with 2-phenylpropionic esters
    Makosza, M
    Surowiec, M
    Paszewski, M
    ARKIVOC, 2004, : 172 - 180
  • [40] Oxidative nucleophilic substitution of hydrogen in nitroarenes with an oxazoline-stabilized carbanion
    Florio, Saverio
    Makosza, Mieczyslaw
    Lorusso, Patrizia
    Troisi, Luigino
    ARKIVOC, 2006, : 59 - 66