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

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2012年 / 143卷

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

页码：130 / 134

页数：5

共 50 条

[21] Tele vs. oxidative substitution of hydrogen in meta monochloromethyl, dichloromethyl, and trichloromethyl nitrobenzenes in the reaction with Grignard reagents
Makosza, M
Varvounis, G
Surowiec, M
Giannopoulo, T
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (19) : 3791 - 3797
[22] Isotope effect in oxidative nucleophilic substitution of hydrogen in nitroarenes
Makosza, M
Stalinski, K
TETRAHEDRON LETTERS, 1998, 39 (21) : 3575 - 3576
[23] Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives
Makosza, M
Stalinski, K
TETRAHEDRON, 1998, 54 (30) : 8797 - 8810
[24] Isotope Effect in Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes
Makosza, M.
Stalinski, K.
Tetrahedron Letters, 39 (21):
[25] Nucleophilic substitution of benzotriazolylalkyl chlorides with Grignard reagents: A direct route to benzotriazoloalkyl(hetero) aromatic compounds
Katritzky, AR
Abdel-Fattah, AAA
Tymoshenko, DO
Belyakov, SA
SYNTHESIS-STUTTGART, 1999, : 1437 - 1440
[26] Substitution of the Nitro Group with Grignard Reagents: Facile Arylation and Alkenylation of Pyridine N-Oxides
Zhang, Fang
Zhang, Song
Duan, Xin-Fang
ORGANIC LETTERS, 2012, 14 (21) : 5618 - 5620
[27] Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents
Shih, Yu-Chiao
Yang, Ya-Ying
Lin, Chun-Chi
Chien, Tun-Cheng
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08): : 4027 - 4036
[28] Nucleophilic aromatic substitution on 1-alkoxy-2-nitronaphthalene by 1-naphthyl Grignard reagents for the synthesis of 2-nitro-1,1′-binaphthyls
Hattori, T
Takeda, A
Yamabe, O
Miyano, S
TETRAHEDRON, 2002, 58 (02) : 233 - 238
[29] Oxidative nucleophilic substitution of hydrogen in nitroarenes. A short review
Makosza, M
Paszewski, M
POLISH JOURNAL OF CHEMISTRY, 2005, 79 (02) : 163 - 178
[30] Oxidative nucleophilic substitution of hydrogen in nitroarenes. A short review
Makosza, M
Stalinski, K
POLISH JOURNAL OF CHEMISTRY, 1999, 73 (01) : 151 - 161

← 1 2 3 4 5 →