Unusual reactivity of 3-chloro-1-pentafluorosulfanylpropene in nucleophilic substitution reactions

被引：20
|
作者：
Trushkov, IV
Brel, VK [1 ]
机构：
[1] Russian Acad Sci, Inst Physiol Act Cpds, Chernogolovka 142432, Russia
[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 28期
关键词：
pentafluorosulfanyl group; nucleophilic substitution; rearrangements;
D O I：
10.1016/j.tetlet.2005.05.041
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 3-chloro-1-pentafluorosulfanylprop-1-ene 1 with KCN yielded the product of prototropic rearrangement CICH=CHCH2SF5, whereas reactions with NaN3 and KSCN gave the SN2 products. Ab initio calculations at MP2/6-311++G** level are used to explain the unusual behaviour of cyanide. It was found that proton transfers from both 1 to CN- and from HCN to the anion of 1 are exothermic. In contrast, azide and thiocyanate ions are too weakly basic to deprotonate 1. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4777 / 4779
页数：3
相关论文
共 50 条
  • [1] Reactivity of a dichlorophosphido complex. Nucleophilic substitution reactions at metal coordinated phosphorus
    Rajagopalan, Rakesh A.
    Jayaraman, Arumugam
    Sterenberg, Brian T.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 761 : 84 - 92
  • [2] Specific features of nucleophilic substitution in 1-chloro-3,4-dinitrobenzene
    N. V. Zotova
    P. M. Kushakova
    V. A. Kuznetsov
    A. A. Rodin
    A. V. Garabadzhiu
    Russian Journal of Organic Chemistry, 2004, 40 : 1473 - 1476
  • [3] Specific features of nucleophilic substitution in 1-chloro-3,4-dinitrobenzene
    Zotova, NV
    Kushakova, PM
    Kuznetsov, VA
    Rodin, AA
    Garahadzhiu, AV
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (10) : 1473 - 1476
  • [4] Reactivity of 3-silyloxy-1,4-enynes: Gold(III)-catalyzed regioselective nucleophilic substitution
    Haug, Timm T.
    Harschneck, Tobias
    Duschek, Alexander
    Lee, Chang-Uk
    Binder, Joerg T.
    Menz, Helge
    Kirsch, Stefan F.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) : 510 - 514
  • [5] Nucleophilic Substitution Reactions of 3-(Bromomethyl)-5,7-dimethyl-2-oxaadamantan-1-ol
    Ivleva, E. A.
    Khatmullina, Yu. E.
    Zaborskaya, M. S.
    Simatova, E. V.
    Bazarova, D. A.
    Klimochkin, Yu. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 60 (04) : 664 - 671
  • [6] 2,3,6-TRIOXYPENTAFULVENES .5(1). REACTIONS WITH PRIMARY AMINES - NUCLEOPHILIC-SUBSTITUTION AND RING EXPANSION
    VICTORY, P
    ALVAREZLARENA, A
    PINIELLA, JF
    GERMAIN, G
    SOLER, E
    MUNOZ, M
    ANALES DE QUIMICA, 1995, 91 (1-2): : 32 - 41
  • [7] Reactions of 3-R-5-nitropyridines with nucleophiles: Nucleophilic substitution vs conjugate addition
    Bastrakov, Maxim A.
    Nikol'skiy, Vladislav V.
    Starosotnikov, Alexey M.
    Fedyanin, Ivan V.
    Shevelev, Svyatoslav A.
    Knyazev, Daniil A.
    TETRAHEDRON, 2019, 75 (47)
  • [8] Nucleophilic Substitution Reactions in the [B3H8]- Anion in the Presence of Lewis Acids
    Shulyak, Alexandra T.
    Bortnikov, Evgeniy O.
    Selivanov, Nikita A.
    Grigoriev, Mikhail S.
    Kubasov, Alexey S.
    Zhdanov, Andrey P.
    Bykov, Alexander Y.
    Zhizhin, Konstantin Y.
    Kuznetsov, Nikolai T.
    MOLECULES, 2022, 27 (03):
  • [9] Nitropyrazoles - 11. Isomeric 1-methyl-3(5)-nitropyrazole-4-carbonitriles in nucleophilic substitution reactions. Comparative reactivity of the nitro group in positions 3 and 5 of the pyrazole ring
    Dalinger, IL
    Zaitsev, AA
    Shkineva, TK
    Shevelev, SA
    RUSSIAN CHEMICAL BULLETIN, 2004, 53 (03) : 580 - 583
  • [10] Nucleophilic substitution and ring transformation reactions with 4-chloro-6-ethyl-3-nitropyrano[3,2-c]quinoline-2,5(6H)-dione
    Hassanin, Hany M.
    ARKIVOC, 2012, : 384 - 397
12345