Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides

Vadim V.Bardin; Alexander M.Maksimov

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Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides

机译：五氟苯磺酰卤对氧化纤维素和有机卤化物的反应性意外区别

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C6F5SO2Cl reacts with organolithiums and organomagnesium halides RM (R=Me, Bu, Ph; M=Li, MgX) to give mainly C6F5H and C6F5Cl. C6F5SO2Br and PhMgBr form C6F5H and (C6F5S)2. This is in contrast to known transformations of them which yield exclusively C6F5SO2Nu under the action of O- and N-nucleophiles. Alternatively, C6F5SO2F is converted to C6F5SO2R and 4-BuC6F4SO2F or 2-PhC6F4SO2Ph under the same conditions. When R=Me, minor amounts of (C6F5SO2)2CH2 and 4-C6F5SO2CH2C6F4SO2F form in addition to C6F5SO2CH3.

机译：C6F5SO 2Cl与有机锂和有机镁卤化物反应RM（R = ME，BU，pH; M = LI，MGX），以主要是C6F5H和C6F5CL。 C6F5SO2BR和PHMGBR形式C6F5H和（C6F5S）2。这与它们的已知转化形成对比，其在O-和N-亲核试剂的作用下仅产生C6F5SO2NU。或者，在相同的条件下，将C6F5SO2F转化为C6F5SO2R和4-BUC6F4SO2F或2-PHC6F4SO2ph。除了C6F5SO 2CH3之外，r = ME，少量（C6F5SO2）2CH2和4-C6F5SO2CH2C6F4SO2F形式。

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来源
《Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences》 |2017年第10期|共7页
作者
Vadim V.Bardin; Alexander M.Maksimov;
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作者单位

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch Russian Academy of Sciences 9 Lavrentiev Ave. 630090 Novosibirsk Russia;

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch Russian Academy of Sciences 630090 Novosibirsk Russia;

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正文语种 eng
中图分类化学;
关键词
C-nucleophiles; organolithium; organomagnesium halides; pentafluorobenzenesulfonyl halides;

机译：C-亲核试剂;有机锂;卤化物卤化物;五氟苯磺酰卤化物;

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专利

1. Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides [J] . Vadim V.Bardin, Alexander M.Maksimov Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences . 2017,第10期

机译：五氟苯磺酰卤对氧化纤维素和有机卤化物的反应性意外区别
2. PREPARATION OF POLYFUNCTIONAL ARYL AND ALKENYL ZINC HALIDES FROM FUNCTIONALIZED UNSATURATED ORGANOLITHIUMS AND THEIR REACTIVITY IN CROSS-COUPLING AND CONJUGATED ADDITION REACTIONS [Review] [J] . Klement I., Tucker CE., Majid TN., Tetrahedron . 1996,第21期

机译：由功能化的不饱和有机硅制备多官能芳基和亚烷基锌的卤化物及其在交叉偶联和共轭加成反应中的反应性[综述]
3. Unexpected reactivity of CH(3,5-Me(2)Pz)(2)(CO)(3)WSnAr3 (Pz = pyrazol-1-yl; Ar = phenyl or p-tolyl) toward hydrogen halide [J] . Tang LF, Hong J, Wen ZK Organometallics . 2005,第18期

机译：CH（3,5-Me（2）Pz）（2）（CO）（3）WSnAr3（Pz =吡唑-1-基; Ar =苯基或对甲苯基）对卤化氢的意外反应性
4. N-Heterocyclic Carbene Adducts of High-Oxidation-State Metal Halides: An Unexpected Instance of Lewis Acidic Ccarbene Character [C] . Mark D. Spicer, Christopher A. Dodds, John P. Culver, American Chemical Society . 2006

机译：高氧化态金属卤化物的N-杂环配子：Lewis酸性Ccarbene特征的意外情况
5. Mechanism of the palladium-catalyzed amination of aryl halides: Kinetic studies of the oxidative addition of aryl halides and sulfonates to phosphine complexes of Pd(0) and of the catalytic reaction of amines with aryl halides and base. [D] . Alcazar-Roman, Luis Manuel. 2001

机译：钯催化芳基卤化物胺化的机理：动力学研究氧化芳基卤化物和磺酸盐到Pd（0）的膦配合物中，以及胺与芳基卤化物和碱的催化反应。
6. Corrigendum: Iron-catalysed cross-coupling of organolithium compounds with organic halides [O] . Zhenhua Jia, Qiang Liu, Xiao-Shui Peng, -1

机译：勘误：铁催化的有机锂化合物与有机卤化物的交叉偶联
7. Unexpected Reactivity of CH(3, 5-Me2Pz)2(CO)3WSnAr3 (Pz = pyrazol-1-yl; Ar = phenyl or p-tolyl) toward Hydrogen Halide [O] . -1

机译：CH（3,5-ME2PZ）2（CO）3WSNAR3（PZ =吡唑-1-基; Ar =苯基或对甲苯基）的意外反应性致卤化物
8. Selective Direct Fluorination of Organolithium and Organomagnesium Compounds [R] . DeYoung, J., Kawa, H., Lagow, R. J. 1992

机译：有机锂和有机镁化合物的选择性直接氟化

Unexpected distinction in reactivity of pentafluorobenzenesulfonyl halides toward organolithiums and organomagnesium halides

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