• Title/Summary/Keyword: Sulfonyl chloride

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Studies on the Perfluoro Alkyl Surfactants(I);Synthesis of Surface Active N-Perfluoroacylmono Aza Crown Ethers (불소계(弗素系) 계면활성제(界面活性劑)에 관한 연구(硏究)(제(第)1보(報));계면활성(界面活性) 함불소계(含弗素系) N-장쇄(長鎖)아실 크라운 에테르유(類)의 합성(合成))

  • Shon, Joo-Whan;Nam, Ki-Dae;Lee, Seung-Yeoll;So, Bu-Young
    • Journal of the Korean Applied Science and Technology
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    • v.7 no.1
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    • pp.49-62
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    • 1990
  • In order to synthesize N,N-di-(polyoxyethylene) perfluoroacyl amines and the surface active monoperfluoroacyl aza crown ethers, it is performed as follow. Six of N,N-di(polyoxyethylene) perfluoro acyl amines were synthesized from perfluoroalkanoic acids with ethanol followed by oxyethylation with triethylene glycol mono chloride or tetra ethylene glycol mono chloride and six of N-perfluor acyl monoaza crown ethers by cyclization of corresponding N,N-di(polyoxy ethylene} perfluoro acyl amines with p-toluene suflonic chloride-NaOH/dioxane, p-toluene sulfonyl chloride KOH/dioxane and benzene sulfonic chloride-KOH/dioxane systems.

Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as Efficient Reagents to Direct Oxidative Conversion of Thiols and Disulfide to Sulfonyl Chlorides

  • Veisi, Hojat;Ghorbani-Vaghei, Ramin;Mahmoodi, Jafar
    • Bulletin of the Korean Chemical Society
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    • v.32 no.10
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    • pp.3692-3695
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    • 2011
  • Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion of sulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through the oxidative chlorination. The overall process is simple, practical, and it provides convenient access to a variety of aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render this method attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides.

Reaction Intermediate of Organic Sulfur Compound Ⅰ. Elimination Mechanism of Sulfonyl Chloride

  • Tae-Seop Uhn;Jong-Pal Lee;Hyun-Seok Park;Hyung-Tae Kim;Zoon-Ha Ryu
    • Bulletin of the Korean Chemical Society
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    • v.11 no.1
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    • pp.60-64
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    • 1990
  • The reactions of alkanesulfonyl chlorides with pyridines in the presence of various solvents have been studied by means of kinetic method. Alkanesulfonyl chlorides bearing ${\alpha}$-hydrogen with the normal attack of pyridine is found to be at the ${\alpha}$-hydrogen with elimination to form the sulfene intermediate evidently. From the mass spectra by the reaction of ethanesulfonyl chloride with 3-picoline in the presence of methanol-$d_1$, it has shown that the reaction has a witness favorable to the slulfene intermediate.

Synthesis of Indoline tri-isopropyl benzene sulfonamide as a potential new asymmetric catalyst (새로운 술폰아미드계의 촉매의 합성)

  • Yun, In-Gwon;Kim, Hwan-Cheol
    • The Journal of Natural Sciences
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    • v.7
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    • pp.47-51
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    • 1995
  • In order to develope new asymmetric catalyst, we synthesized the following new sulfonamide derivatives start from S-Indoline-2-Carboxylic Acid via the following 5 steps. Hydroxy methyl derivative(1) was thus treated with methane sulfonyl chloride in the presence of triethylamine as base to give mesylated derivative(2) in 85% of isolated yield. The mesylate compound (2) was treated with excess sodium azide to give Azido derivative (4) in 95% isolated yield. Azido compound (3) was then reduced to the corresponding amino derivative in near quntitative yield by the hydrogenation under hydrogen atmospere in the presence of catalytic amount of Pd-C. The amino derivative (4) was converted to its sulfonamide derivatives by the treatment of compound(4) with triisopropyl benzene sulfonyl chloride in the presence of triethyl amine as base. Finally t-BOC group of the compound(5) was removed by the treatement of excess Trifluoro-acetic acid in near quantitative yield to give the target sulfonamide derivative (7) .in this paper we prepared compound(6) in 49% overall yield via the 5 steps of synthesis starting from t-Boc- 2-hydroxy methyl indoline(1) which cab be easily prepared from commercial available S-indoline-2-carboxylic acid by known methods. we plan to apply this new catalyst for the asymmetric reduction , diels-alder reaction, aldolcondensation reaction in due courses.

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Solvent Effect on the Nucleophilic Substitution Reaction of Naphthalene Sulfonyl Chloride with Pyridine (염화나프탈렌술포닐과 피리딘의 친핵성 치환반응에 대한 용매효과)

  • Ikchoon Lee;Tae Seop Uhm;Dae Dong Sung;Geol Yeom
    • Journal of the Korean Chemical Society
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    • v.27 no.1
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    • pp.1-8
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    • 1983
  • Solvent effects on nucleophilic substitution reaction of naphthalene sulfonyl chlorides with pyridine in protic and aprotic solvent have been studied by means of conductometry. Results showed that the rate constants increased with dielectric constants for protic solvents, while they decreased with dielectric constants for aprotic solvents, except for acetonitrile which has a higher dielectric constant but had also greater rate constant. The rate constants were shown to be more susceptible to polarity-polarizability parameter, , than to hydrogen bond donor acidity parameter, ${\alpha}$, indicating that the pulling effect of hydrogen bonding solvent.

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