1,721,048 research outputs found

    Anion nucleophilicity in ionic liquids: a comparison with traditional molecular solvents of different polarity

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    The nucleophilic reactivity of a homogeneous series of anions (halides, pseudohalides and organic anions) in the ionic liquids [hexmim] [ClO4] and [hexmim] [PF6] has been measured in their reaction with n-alkyl methanesulfonates, and compared with that found in traditional molecular solvents of different polarity, that is, chlorobenzene, DMSO, and MeOH. (c) 2005 Elsevier Ltd. All rights reserved

    Naked anion effect

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    TETRABUTYLAMMONIUM FLUORIDE - A POWERFUL CATALYST FOR THE REGIOSELECTIVE OPENING OF EPOXIDES WITH THIOLS

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    Tetrabutylammonium fluoride (1) catalyses under mild conditions the opening of epoxides 2a-k with thiols 3-6 to produce the corresponding beta-hydroxy thioethers 7-11 in excellent yields (88-100%) and with high regioselectivity. Furthermore, O-protected glycidols react without any loss of the protective group

    REGIOSELECTIVE CONVERSION OF O-PROTECTED GLYCIDOLS TO FLUOROHYDRINS CATALYZED BY TETRABUTYLAMMONIUM DIHYDROGENTRIFLUORIDE UNDER SOLID-LIQUID PTC CONDITIONS

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    A number of O-protected glycidols are regioselectively converted into the corresponding fluorohydrins FCH2CH(OH)CH2OX by reaction with catalytic amounts of Bu4N+H2F3- and a molar excess of KHF2. Most of the protective groups (X) examined are stable under the above conditions, moreover stereogenic carbons are not affected

    SYNTHESIS OF PENTACOORDINATED TETRAALKYLAMMONIUM AND TETRAALKYLPHOSPHONIUM DIFLUOROSILICATES

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    Several quaternary onium difluorosilicates 3, R(2)(1)R(2)SiF(2)(-) Q(+) (Q = R(3)(3)R(4)N(+), R(3)(3)R(4)P(+)), have been prepared by reaction of a trisubstitued silane I, R(2)(1)R(2)SiH, and an onium hydrogendifluoride 2, Q(+) HF2-, in benzene. The products 3 are isolated in very good yields (92-98%) and purity (> 99%)

    TCT-catalyzed Beckmann rearrangement of ketoximes in biodegradable ionic liquids

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    Imidazolium-based ionic liquids (ILs) containing ester moieties in the side chain were successfully used as an alternative to traditional ILs in the Beckmann rearrangement of ketoximes catalyzed by 2,4,6-trichloro[1,3,5]triazine. The procedure is mild and suitable for both aromatic and cycloaliphatic substratesaffording the rearrangement products in good to quantitative yields. The process is eco-sustainable since these ILs are biodegradable and in addition they can be recovered and reused

    Regioselective opening of epoxides to beta-amido alcohols under solid-liquid PTC conditions

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    A study on the ring opening of a number of epoxides 1 with trifluoroacetamide (2) under solid-liquid phase transfer catalysis (SL-PTC) conditions has been performed. The reaction is completely regioselective affording beta-amido alcohols 3 deriving from the attack of the nucleophile to the less substituted carbon atom of the oxirane ring. (C) 1997 Elsevier Science Ltd

    Novel concise synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines by ring opening of glycidols under solid-liquid phase transfer catalysis conditions

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    The ring opening of glycidols with N-(2-fluorophenyl)toluene-p-sulfonamide under SL-PTC conditions, followed by ring closure with (BuOK)-O-t, provides a novel high yielding synthesis of 2-substituted 3,4-dihydro-2H-1,4-benzoxazines
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