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Journal articles on the topic 'Solvolytic Reactions'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Kevill, Dennis N., Byoung-Chun Park, and Jin Burm Kyong. "Evidence for general base catalysis by protic solvents in a kinetic study of alcoholyses and hydrolyses of 1-(phenoxycarbonyl)pyridinium ions under both solvolytic and non-solvolytic conditions." Collection of Czechoslovak Chemical Communications 74, no. 1 (2009): 43–55. http://dx.doi.org/10.1135/cccc2008164.

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The kinetics of nucleophilic substitution reactions of 1-(phenoxycarbonyl)pyridinium ions, prepared with the essentially non-nucleophilic/non-basic fluoroborate as the counterion, have been studied using up to 1.60 M methanol in acetonitrile as solvent and under solvolytic conditions in 2,2,2-trifluoroethan-1-ol (TFE) and its mixtures with water. Under the non- solvolytic conditions, the parent and three pyridine-ring-substituted derivatives were studied. Both second-order (first-order in methanol) and third-order (second-order in methanol) kinetic contributions were observed. In the solvolysi

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2

Popsavin, Velimir, Mirjana Popsavin, and Dusan Miljkovic. "S-O acetyl rearrangement in 6-thio-D-glucose derivatives." Journal of the Serbian Chemical Society 83, no. 12 (2018): 1297–303. http://dx.doi.org/10.2298/jsc180811075p.

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The solvolytic reaction of 1,2-O-isopropylidene-3,6-di-O-(p-toluenesulphonyl)- ?-D-glucofuranose (2), as well as that of 6-chloro-6-deoxy-1,2-O-isopropylidene-3-O-(p-toluenesulphonyl)-?-D-glucofuranose (3), in the presence of potassium thioacetate unexpectedly gave the 6-S-acetyl-5-O-acetyl derivative 5 as the main reaction product. A possible mechanism of these transformations was postulated whereby the main role was ascribed to a neighbouring group participation process, involving hydrogen thio-orthoester formation as an intermediate. The regiospecific monosubstitution of the 6-tosyloxy grou

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3

Mollin, Jiří, Pavlína Staňková, and Oldřiška Staňková. "The evidence and applications of equilibria between hydroxide and alkoxide ions in aqueous-alcoholic systems." Collection of Czechoslovak Chemical Communications 55, no. 11 (1990): 2614–23. http://dx.doi.org/10.1135/cccc19902614.

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The composition of solvolysis products of butyl bromide, acetanhydride, and benzoyl chloride has been followed aqueous alcohol in alkaline and (except for butyl bromide) also in neutral regions. The results have been used as a piece of evidence of the existence of equilibrium between hydroxide and alkoxide ions and for evaluation of the possibility of calculation of the concentration ratio of hydroxide and alkoxide ions from the concentration ratios of the products as well as for evaluation of selectivities of the solvolytic reactions for mechanistic purposes.

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4

Creary, Xavier, Vincent P. Casingal, and Charlene E. Leahy. "Solvolytic elimination reactions. Stepwise or concerted?" Journal of the American Chemical Society 115, no. 5 (1993): 1734–38. http://dx.doi.org/10.1021/ja00058a018.

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5

Park, Kyoung-Ho, Chan Joo Rhu, Jin Burm Kyong, and Dennis N. Kevill. "The Effect of the ortho Nitro Group in the Solvolysis of Benzyl and Benzoyl Halides." International Journal of Molecular Sciences 20, no. 16 (2019): 4026. http://dx.doi.org/10.3390/ijms20164026.

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A kinetic study was carried out on the solvolysis of o-nitrobenzyl bromide (o-isomer, 1) and p-nitrobenzyl bromide (p-isomer, 3), and o-nitrobenzoyl chloride (o-isomer, 2) in a wide range of solvents under various temperatures. In all of the solvents without aqueous fluoroalcohol, the reactions of 1 were solvolyzed at a similar rate to those observed for 3, and the reaction rates of 2 were about ten times slower than those of the previously studied p-nitrobenzoyl chloride (p-isomer, 4). For solvolysis in aqueous fluoroalcohol, the reactivity of 2 was kinetically more reactive than 4. The l/m v

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6

Thibblin, Alf. "Mechanisms of solvolytic alkene-forming elimination reactions." Chemical Society Reviews 22, no. 6 (1993): 427. http://dx.doi.org/10.1039/cs9932200427.

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7

CREARY, X., V. P. CASINGAL, and C. E. LEAHY. "ChemInform Abstract: Solvolytic Elimination Reactions. Stepwise or Concerted?" ChemInform 24, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199327089.

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8

Meng, Qingshui, and Alf Thibblin. "Mechanisms of solvolytic elimination reactions of tertiary substrates: stereospecific 1,2-elimination reactions." Journal of the Chemical Society, Perkin Transactions 2, no. 7 (1999): 1397–404. http://dx.doi.org/10.1039/a901296f.

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9

Smith, Peter James, and Jyotsna Pradhan. "Solvolysis of 2-substituted-9-(otrho-substituted phenylmethyl)fluoren-9-yltrimethylammonium ions in various solvents. The effect of steric crowding on alkene formation." Canadian Journal of Chemistry 64, no. 6 (1986): 1060–71. http://dx.doi.org/10.1139/v86-178.

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The solvolytic reaction of several 9-(ortho-substituted phenylmethyl)fluoren-9-yltrimethylammonium salts has been investigated in several different solvents. Substitution and elimination products were found for the reactions in all the solvents studied, with the exceptions that reaction in both tert-butyl alcohol and chloroform led exclusively to the alkene product. The observed rate constants for alkene formation and the percent alkene were measured and it was found that the di-ortho compounds reacted at a faster rate but produced less alkene than the reaction of the corresponding mono-ortho

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10

Creary, Xavier, Holia N. Hatoum, Angela Barton, and Timothy E. Aldridge. "Solvolytic elimination reactions of tertiary .alpha.-CSNMe2-substituted systems." Journal of Organic Chemistry 57, no. 6 (1992): 1887–97. http://dx.doi.org/10.1021/jo00032a051.

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11

KITAMURA, T., H. TANIGUCHI, and Y. TSUNO. "ChemInform Abstract: Solvolytic Generation and Reactions of Vinyl Cations." ChemInform 29, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199847313.

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12

Kummer, D., S. H. Abdel Halim, and M. F. El-Shahat. "Solvolytic and Thermolytic Reactions of Heterocyclic Pentacoordinate Silicon Compounds." Zeitschrift f�r anorganische und allgemeine Chemie 622, no. 10 (1996): 1701–4. http://dx.doi.org/10.1002/zaac.19966221012.

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13

Gonçalves, Raquel M. C., and Lídia M. P. C. Albuquerque. "Application of correlation analysis to solvolytic reactions of tertiary haloalkanes and Menschutkin reactions." Journal of Physical Organic Chemistry 14, no. 11 (2001): 731–36. http://dx.doi.org/10.1002/poc.426.

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14

Kevill, Dennis N., and Zoon Ha Ryu. "Rate and Product Studies in the Solvolyses of Two Arenesulfonic Anhydrides." Journal of Chemical Research 2007, no. 6 (2007): 365–69. http://dx.doi.org/10.3184/030823407x218084.

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The specific rates of solvolysis of benzenesulfonic anhydride (1) and p-toluenesulfonic anhydride (2) have been measured conductometrically at −10°C in 34 solvents for 1 and 33 solvents for 2. Studies at higher temperatures have allowed extrapolated values in additional solvents to be calculated. All of the values, for 35 solvents for 1 and for 37 solvents for 2, have been used in an extended Grunwald–Winstein equation treatment using NT and YOTs values. Activation parameters in several solvents and kinetic solvent isotope effects (MeOH/MeOD) have been determined for both substrates. Product s

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15

Thibblin, Alf, and Yoshihiro Saeki. "Ion−Molecule Pairs in Leaving-Group-Promoted Solvolytic Elimination Reactions." Journal of Organic Chemistry 62, no. 4 (1997): 1079–82. http://dx.doi.org/10.1021/jo9619645.

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16

Park, Kyoung Ho, Mi Hye Seong, Jin Burm Kyong, and Dennis N. Kevill. "Rate and Product Studies with 1-Adamantyl Chlorothioformate under Solvolytic Conditions." International Journal of Molecular Sciences 22, no. 14 (2021): 7394. http://dx.doi.org/10.3390/ijms22147394.

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A study was carried out on the solvolysis of 1-adamantyl chlorothioformate (1-AdSCOCl, 1) in hydroxylic solvents. The rate constants of the solvolysis of 1 were well correlated using the Grunwald–Winstein equation in all of the 20 solvents (R = 0.985). The solvolyses of 1 were analyzed as the following two competing reactions: the solvolysis ionization pathway through the intermediate (1-AdSCO)+ (carboxylium ion) stabilized by the loss of chloride ions due to nucleophilic solvation and the solvolysis–decomposition pathway through the intermediate 1-Ad+Cl− ion pairs (carbocation) with the loss

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17

Gharbi-Benarous, Josyane, Mounir M. Essayegh та Gilbert Dana. "Réactivité des α-halobutyrolactones à halogènes tertiaires vis-à-vis des nucléophiles faiblement basiques". Canadian Journal of Chemistry 65, № 9 (1987): 2031–38. http://dx.doi.org/10.1139/v87-338.

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2-Methyl-4-phenylbutenolide (5) is prepared in a quantitative manner by an elimination of HBr from the corresponding bromolactones 3. This reaction, induced by halide ions at 100 °C in polar aprotic solvents (DMF, DMSO), is accompanied by a bimolecular nucleophilic substitution. In these reactions, the solvent seems able to play an active role. A polar solvent induces the necessary activation of the substrate (by a prior strong polarization of the C—Br bond). In the absence of halide ions, a solvolytic reaction takes place. As soon as the elimination reaction produces enough halide ions, the b

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18

Goncalves, Raquel M. C., and Lidia M. P. C. Albuquerque. "ChemInform Abstract: Application of Correlation Analysis to Solvolytic Reactions of Tertiary Haloalkanes and Menschutkin Reactions." ChemInform 33, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.200217290.

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19

Hertzberg, Sissel, Hanny Berger, and Synnøve Liaaen-Jensen. "Carotenoid Sulfates. 5. Preparation and Solvolytic Reactions of Unstable Carotenoid Sulfates." Acta Chemica Scandinavica 39b (1985): 725–34. http://dx.doi.org/10.3891/acta.chem.scand.39b-0725.

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20

Kohout, Ladislav, Vijay Kumar Sethi, Jaroslav Zajíček та Alexander Kasal. "Solvolytic reactions of empiric 3-methanesulfonyloxy-7-benzoyloxy-5β,6β-cyclopropanocholestanes". Collection of Czechoslovak Chemical Communications 51, № 2 (1986): 436–46. http://dx.doi.org/10.1135/cccc19860436.

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Acetolysis of 3-methanesulfonyloxy-7-benzoyloxy-5β,6β-cyclopropanocholestanes with various configurations in positions 3 and 7 is described and the products are assigned structure using spectral methods. The 7-substituted compounds show greater propensity to elimination reactions than the 7-unsubstituted ones.

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21

Kohout, Ladislav. "Solvolytic reactions of epimeric 3-methanesulfonyloxy-7-benzoyloxy-5α,6α-cyclopropanocholestanes". Collection of Czechoslovak Chemical Communications 51, № 10 (1986): 2222–31. http://dx.doi.org/10.1135/cccc19862222.

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Acetolysis of all possible configurational isomers of 3-methanesulfonyloxy-7-benzoyloxy-5α,6α-cyclopropanocholestanes is described and structure of the acetolysis products determined by spectroscopic methods. The 7-substituted derivatives show a greater propensity to elimination reactions than the 7-unsubstituted compounds.

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22

Maskill, H. "Concurrent solvolytic and non-solvolytic reactions of benzyl azoxytoluene-p-sulphonate in aqueous trifluoroethanol containing bases: an unprecedented mechanistic duality." Journal of the Chemical Society, Chemical Communications, no. 18 (1986): 1433. http://dx.doi.org/10.1039/c39860001433.

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23

Bentley, T. William, Gareth Llewellyn, and Zoon Ha Ryu. "Solvolytic Reactions in Fluorinated Alcohols. Role of Nucleophilic and Other Solvation Effects." Journal of Organic Chemistry 63, no. 14 (1998): 4654–59. http://dx.doi.org/10.1021/jo980109d.

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24

Meng, Qingshui, Adolf Gogoll, and Alf Thibblin. "Concerted and Stepwise Solvolytic Elimination and Substitution Reactions: Stereochemistry and Substituent Effects." Journal of the American Chemical Society 119, no. 6 (1997): 1217–23. http://dx.doi.org/10.1021/ja962469t.

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25

March, J. G., J. K. Amartey, and W. Wolf. "Ligand exchange and solvolytic reactions of99mTcBr 6 2− in non-aqueous media." Journal of Radioanalytical and Nuclear Chemistry Articles 132, no. 2 (1989): 293–303. http://dx.doi.org/10.1007/bf02136088.

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26

Takeuchi, K. "Structural modification and solvent interactions in solvolytic reactions of open-chain compounds." Pure and Applied Chemistry 70, no. 10 (1998): 2023–30. http://dx.doi.org/10.1351/pac199870102023.

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27

Sunko, Dionis E., Branko Jursic, and Mladen Ladika. "Leaving group rate ratios in solvolytic displacement reactions. Effect of neighboring sulfur." Journal of Organic Chemistry 52, no. 11 (1987): 2299–301. http://dx.doi.org/10.1021/jo00387a036.

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28

Meng, Qingshui, and Alf Thibblin. "Borderline Solvolytic Reactions. Appearance of Solvent-Promoted E2 Reaction in Competition with Stepwise Elimination and Substitution Reactions." Journal of the American Chemical Society 117, no. 6 (1995): 1839–40. http://dx.doi.org/10.1021/ja00111a026.

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29

China, Hideyasu, Nami Kageyama, Hotaka Yatabe, Naoko Takenaga, and Toshifumi Dohi. "Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions." Molecules 26, no. 7 (2021): 1897. http://dx.doi.org/10.3390/molecules26071897.

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We report a convenient and practical method for the preparation of nonexplosive cyclic hypervalent iodine(III) oxidants as efficient organocatalysts and reagents for various reactions using Oxone® in aqueous solution under mild conditions at room temperature. The thus obtained 2-iodosobenzoic acids (IBAs) could be used as precursors of other cyclic organoiodine(III) derivatives by the solvolytic derivatization of the hydroxy group under mild conditions of 80 °C or lower temperature. These sequential procedures are highly reliable to selectively afford cyclic hypervalent iodine compounds in exc

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30

García-Río, L., J. R. Leis, and C. Reigosa. "Reactivity of Typical Solvolytic Reactions in SDS and TTABr Water-in-Oil Microemulsions." Journal of Physical Chemistry B 101, no. 28 (1997): 5514–20. http://dx.doi.org/10.1021/jp970460n.

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31

Thibblin, Alf. "Deprotonation of ions pairs in aqueous solvent. Competing bimolecular and solvolytic elimination reactions." Journal of the American Chemical Society 109, no. 7 (1987): 2071–76. http://dx.doi.org/10.1021/ja00241a026.

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32

Zeng, Xiaofeng, and Alf Thibblin. "Competing solvolytic elimination and substitution reactions via very short-lived ion-pair intermediates." Journal of the Chemical Society, Perkin Transactions 2, no. 9 (2001): 1600–1607. http://dx.doi.org/10.1039/b102869n.

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33

Puri, J. K., Jaswinder Kaur, Vijay Sharma, and Jack M. Miller. "Preparation of metal bromoacetates from other salts by Solvolytic reactions in fused monobromoacetic acid." Polyhedron 4, no. 7 (1985): 1253–57. http://dx.doi.org/10.1016/s0277-5387(00)84113-3.

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34

Meng, Qingshui, and Alf Thibblin. "Stepwise and Concerted Solvolytic Elimination and Substitution Reactions: E1 Reaction via a Primary Carbocation." Journal of the American Chemical Society 119, no. 21 (1997): 4834–40. http://dx.doi.org/10.1021/ja970362f.

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35

OKAMOTO, K. "ChemInform Abstract: Generation and Ion-Pair Structures of Unstable Carbocation Intermediates in Solvolytic Reactions." ChemInform 22, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199125273.

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36

Takeuchi, Ken'ichi. "ChemInform Abstract: Structural Modification and Solvent Interactions in Solvolytic Reactions of Open-Chain Compounds." ChemInform 30, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199928327.

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37

SHINER, V. J. JUN, and F. P. WILGIS. "ChemInform Abstract: Heavy Atom Isotope Rate Effects in Solvolytic Nucleophilic Reactions at Saturated Carbon." ChemInform 24, no. 32 (2010): no. http://dx.doi.org/10.1002/chin.199332297.

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38

Jurić, Sandra, and Olga Kronja. "Lack of the neighboring group rate effect in solvolytic reactions that proceed via participation." Journal of Physical Organic Chemistry 21, no. 2 (2008): 108–11. http://dx.doi.org/10.1002/poc.1290.

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39

Bellagamba, Vera, Roberta Ercoli, Aido Gamba, and Massimo Simonetta. "Theoretical investigation on the role of solvent in solvolytic reactions. Part 7. The enhancement of solvolysis of fluoromethane viewed by Voronoi polyhedra." Journal of the Chemical Society, Perkin Transactions 2, no. 8 (1986): 1127. http://dx.doi.org/10.1039/p29860001127.

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40

Morzycki, Jacek W. "Vitamin D relatives. Part I. B-thiophene-des-A-cholestanes. Solvolytic reactions of some derivatives of 2,2-disubstituted cyclohexane-1,4-diol and 4-hydroxycyclohexan-1-one." Canadian Journal of Chemistry 64, no. 8 (1986): 1536–39. http://dx.doi.org/10.1139/v86-252.

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Some derivatives of des-A-cholestane with a thiophene ring B have been prepared from triketone 2. The reactions of tosylates of C-10 alcohols (7b, 9b, and 8c) leading to A-ring ethers (10 and 11) and olefin 5, respectively, have been studied. The solvolysis of tosylate 4c and the Bamford–Stevens reactions of p-tosylhydrazones 3c and 13b are also discussed.

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41

Faza, Olalla Nieto, Carlos Silva López, Rosana Álvarez, and Ángel R. de Lera. "Solvolytic Ring-Opening Reactions of Cyclopropyl Bromides. An Assessment of the Woodward−Hoffmann−DePuy Rule." Journal of Organic Chemistry 69, no. 26 (2004): 9002–10. http://dx.doi.org/10.1021/jo0487294.

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42

Meng, Qingshui, and Alf Thibblin. "Solvent-Promoted E2 Reaction Competing with SN2 Reaction and Stepwise Solvolytic Elimination and Substitution Reactions." Journal of the American Chemical Society 117, no. 37 (1995): 9399–407. http://dx.doi.org/10.1021/ja00142a003.

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43

Puri, J. K., and Jack M. Miller. "Solvolytic reactions of Lewis acids in dibromoacetic acid and the characterization of the solvolysed products." Inorganica Chimica Acta 101, no. 2 (1985): 135–40. http://dx.doi.org/10.1016/s0020-1693(00)85999-x.

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44

Puri, J. K., V. K. Vats, Humayun Mandal, and Jack M. Miller. "Solvolytic reactions of Lewis acids in monobromoacetic acid and the nature of the solvolysed products." Inorganica Chimica Acta 97, no. 2 (1985): 205–10. http://dx.doi.org/10.1016/s0020-1693(00)86586-x.

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45

Sidhu, Harvinder, and Alf Thibblin. "Competing solvolytic substitution and elimination reactions via a common irreversibly formed ion-molecule pair intermediate." Journal of Physical Organic Chemistry 7, no. 10 (1994): 578–84. http://dx.doi.org/10.1002/poc.610071009.

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46

THIBBLIN, A. "ChemInform Abstract: Ion Pairs and Ion-Molecule Pairs in Solvolytic Substitution, Elimination and Rearrangement Reactions." ChemInform 26, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199546281.

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47

Brown, Herbert C., Irvin Rothberg, and J. Chandrasekharan. "Structural effects in solvolytic reactions. 51. Examination of the differences in the behavior of secondary and tertiary U-shaped bicyclic derivatives toward solvolysis." Journal of Organic Chemistry 50, no. 26 (1985): 5574–77. http://dx.doi.org/10.1021/jo00350a028.

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48

Thring, Ronald W., Esteban Chornet, Jean Bouchard, Pierre F. Vidal, and Ralph P. Overend. "Characterization of lignin residues derived from the alkaline hydrolysis of glycol lignin." Canadian Journal of Chemistry 68, no. 1 (1990): 82–89. http://dx.doi.org/10.1139/v90-017.

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Lignin residues from the alkaline hydrolysis of solvolytic lignin have been characterized by elemental analysis, size exclusion chromatography, Fourier transform infrared spectroscopy, 13C NMR, and for methoxyl content. All lignin residues were found to have higher carbon and lower oxygen contents than the original glycol lignin. Methoxyl contents decreased with increasing severity of treatment. All treated lignins have lower molecular weights than the original, which is indicative of the extensive depolymerization of glycol lignin by alkaline hydrolysis. The appearance of new bands in the 305

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49

D'Souza, Malcolm, and Dennis Kevill. "Influence of Sulfur for Oxygen Substitution in the Solvolytic Reactions of Chloroformate Esters and Related Compounds." International Journal of Molecular Sciences 15, no. 10 (2014): 18310–32. http://dx.doi.org/10.3390/ijms151018310.

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50

Bellagamba, Vera, Roberta Ercoli, Aldo Gamba, and Massimo Simonetta. "A theoretical investigation on the role of solvent in solvolytic reactions. Part 7. CH2LiF in Water." Journal of the Chemical Society, Perkin Transactions 2, no. 2 (1985): 185. http://dx.doi.org/10.1039/p29850000185.

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