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Journal articles on the topic 'Solvolysis reactions'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

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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2

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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3

D’Souza, Malcolm J., and Dennis N. Kevill. "Mechanistic studies of the solvolysis of alkanesulfonyl and arenesulfonyl halides." Beilstein Journal of Organic Chemistry 18 (January 17, 2022): 120–32. http://dx.doi.org/10.3762/bjoc.18.13.

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There have been several studies on the solvolysis mechanisms for alkanesulfonyl chlorides (RSO2Cl) and arenesulfonyl chlorides (ArSO2Cl). The earlier of these studies were reviewed a little over thirty years ago by Gordon, Maskill and Ruasse (Chem. Soc. Rev. 1989, 18, 123–151) in a contribution entitled “Sulfonyl Transfer Reactions”. The present review will emphasize more recent contributions and, in particular, the application of the extended Grunwald–Winstein equation and kinetic solvent isotope effects to the solvolysis reactions. There is also an appreciable number of reports concerning th

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4

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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5

Bremner, JB, and KN Winzenberg. "Cyanogen-Bromide-Mediated and Methyl-Chloroformate-Mediated Synthesis of Some [3]Benzazonino[8,7,6-abc]Carbazole, [3]Benzazecino[9,8,7-abc]Carbazole, Naphth[1,8,7-def]Azonine and Naphth[1,8,7-def]Azecine Derivatives." Australian Journal of Chemistry 39, no. 1 (1986): 1. http://dx.doi.org/10.1071/ch9860001.

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Reaction of 7,8-dimethoxy-1,4,5,9,13c,13d-hexahydro-2H-indolo [3′,2′:4,5] indolo [1,7,6-aji] isoquinoline (4a) and 8,9-dimethoxy- 1,2,3,5,6,10,14c,14d-octahydro-indolo[3′,2′:3,4] naphtho [2,1,8-ija] quinolizine (4b) with cyanogen bromide in the presence of potassium carbonate afforded the elimination products 7,8-dimethoxy-1,2,3,4,5,9- hexahydro [3] benzazonino [8,7,6-abc]carbazole-3-carbonitrile (5a) and 8,9-dimethoxy-2,3,4,5,6,10-hexahydro-1H-[3] benzazecino [9,8,7-abc]carbazole-4-carbonitrile (5b) in 4% and 88% yield respectively; 7- (2-bromo)ethyl-1,2-dimethoxy-4,5,6,6a,7,12-hexahydroisoqu

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6

Kumaniaev, Ivan, Elena Subbotina, Maxim V. Galkin, et al. "A combination of experimental and computational methods to study the reactions during a Lignin-First approach." Pure and Applied Chemistry 92, no. 4 (2020): 631–39. http://dx.doi.org/10.1515/pac-2019-1002.

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AbstractCurrent pulping technologies only valorize the cellulosic fiber giving total yields from biomass below 50 %. Catalytic fractionation enables valorization of both cellulose, lignin, and, optionally, also the hemicellulose. The process consists of two operations occurring in one pot: (1) solvolysis to separate lignin and hemicellulose from cellulose, and (2) transition metal catalyzed reactions to depolymerize lignin and to stabilized monophenolic products. In this article, new insights into the roles of the solvolysis step as well as the operation of the transition metal catalyst are gi

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7

Huang, Xicai, and Andrew J. Bennet. "Kinetic evidence for the importance of solvent-separated ion pairs during the solvolyses of adamantylideneadamantyl derivatives." Canadian Journal of Chemistry 82, no. 9 (2004): 1336–40. http://dx.doi.org/10.1139/v04-101.

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The aqueous ethanolysis reactions of adamantylideneadamantyl tosylate, -bromide, and -iodide (1-OTs, 1-Br and 1-I) were monitored as a function of ionic strength. Special salt effects are observed during the solvolyses of both homoallylic halides, but not in the case of the tosylate 1-OTs. The measured α-secondary deuterium kinetic isotope effects for the solvolysis of 1-Br in 80:20 and 60:40 v/v ethanolwater mixtures at 25 °C are 1.110 ± 0.018 and 1.146 ± 0.009, respectively. The above results are consistent with the homoallylic halides reacting via a virtual transition state in which both f

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8

Mayr, Herbert, and Armin R. Ofial. "How to predict changes in solvolysis mechanisms." Pure and Applied Chemistry 81, no. 4 (2009): 667–83. http://dx.doi.org/10.1351/pac-con-08-08-26.

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Stopped-flow and laser flash techniques have been employed to investigate the individual steps of the solvolysis reactions of benzhydryl (diarylmethyl) halides and carboxylates. In this way, absolute rate constants for the ionization (k1), recombination of the carbocation with the leaving group (k-1), and subsequent reaction with the solvent (kSolvOH) have been determined. As the stabilization of the carbocations increases, the mechanism changes from (a) SN1 reactions with irreversible ionization through (b) SN1 reactions with common-ion return and (c) SN2C+ reactions, where the intermediate c

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9

Ion, Ganescu, Bratulescu George, Papa Ion, Ganescu Anca, Chirigiu Liviu, and Barbu Alin. "Solvolysis of the [Cr(NCS)4(benztriazole)2]- ion in ethanol-water mixtures." Journal of Indian Chemical Society Vol. 79, Aug 2002 (2002): 649–54. https://doi.org/10.5281/zenodo.5843274.

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Faculty of Chemistry, University of Craiova, 13 A. I. Cuza Str., 1100 Craiova. Romania <em>Fax : </em>4-051-197048 Faculty of Pharmacy, University of Medicine and Pharmacy. Bdl. I. Antonescu, 94 Craiova, Romania <em>Manuscript received 5 November 2001. revised 8 March 2002. accepted 21 March 2002</em> Measuring the concentration of the free thiocyanate ion and the nontransformed [Cr(NCS)<sub>4</sub>(benztriazole)<sub>2</sub>]<sup>-</sup> ion, the rate constants of the solvolysis process have been calculated. The solvolysis includes two parallel reactions - the substitution of thiocyanate ions

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10

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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11

Conner, John K., Johanna Haider, MN Stuart Hill, Howard Maskill, and Monique Pestman. "The mechanism of solvolysis of 2-adamantyl azoxytosylate: isotopic labelling, medium effect, and attempted deoxygenation studies." Canadian Journal of Chemistry 76, no. 6 (1998): 862–68. http://dx.doi.org/10.1139/v98-071.

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Rates of solvolysis of 2-adamantyl azoxytosylate (1) have been measured over a range of temperatures in ethanoic acid, methanoic acid, 50:50 (v/v) trifluoroethanol:water, 80:20 (v/v) trifluoroethanol:water, 97:3 (w/w) trifluoroethanol:water, and 70:30 (v/v) ethanol:water. For comparison, rates of solvolysis of 2-adamantyl tosylate (2) have also been measured in 50:50, 80:20, and 90:10 (v/v) trifluoroethanol:water, and for both compounds, activation parameters have been determined. These and results published earlier allow a correlation of the two reactions and indicate that the m value for 2-a

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12

Stein, Allan R. "β-Deuterium kinetic isotope effects for identity processes: bromide ion substitution at 1-bromo-1-arylethanes and 2-bromooctane". Canadian Journal of Chemistry 72, № 8 (1994): 1789–96. http://dx.doi.org/10.1139/v94-227.

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While deuterium kinetic isotope effects for solvolyses have been extensively studied, other nucleophilic substitutions have received less attention, and identity processes, that is, substitutions where the nucleophile and leaving group are the same, have rarely been examined. Identity reactions must pass through a truly symmetrical stage, a transition state or an intermediate, so that data will be of interest to both theoretical and experimental chemists. Values of kH/kD have been determined by polarimetry for bromide exchange– racemization at ArCHBrCH3/CD3 (Ar = C6H5,4-Br- and 4-Me-C6H4, and

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13

Schaller, HeikeâF, and Herbert Mayr. "âCarbocation Watchingâ in Solvolysis Reactions." Angewandte Chemie International Edition 47, no. 21 (2008): 3958–61. http://dx.doi.org/10.1002/anie.200800354.

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14

V., Jagannadham. "Substituent effects on the spontaneous cleavage of α-alkyl/phenyl benzyl-gemdichlorides in aqueous solution". Journal of Indian Chemical Society Vol. 84, Sep 2007 (2007): 937–38. https://doi.org/10.5281/zenodo.5827341.

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Department of Chemistry, Osmania University, Hyderabad-500 007, India <em>E-mail</em> : vjchem@osmania.ac.in <em>Manuscript received 7 December 2006, accepted 25 June 2007</em> The solvolysis reactions of a-alkyl/phenyl benzyl-<em>gem</em>-dichlorides in water proceed by a stepwise mechanism through α-chloro-α-alkyl/phenyl benzyl carbocation intermediates, which are captured by water with a rate constant <em>k<sub>s </sub></em>(s<sup>-1</sup>) to give the corresponding carbonyl compounds as the sole detectable products.

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15

Kang, Naixin, Changlong Wang, and Didier Astruc. "Hydrogen Evolution upon Ammonia Borane Solvolysis: Comparison between the Hydrolysis and Methanolysis Reactions." Chemistry 5, no. 2 (2023): 886–99. http://dx.doi.org/10.3390/chemistry5020060.

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Hydrogen (H2) production is a key challenge for green carbon-free sustainable energy. Among the H2 evolution methods from H-rich materials, ammonia borane (AB) solvolysis stands as a privileged source under ambient and sub-ambient conditions given its stability, non-toxicity, and solubility in protic solvents, provided suitable and optimized nanocatalysts are used. In this paper dedicated to Prof. Avelino Corma, we comparatively review AB hydrolysis and alcoholysis (mostly methanolysis) in terms of nanocatalyst performances and discuss the advantages and inconveniences of these two AB solvolys

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16

Qin, Qi, Youwei Xie, and Paul E. Floreancig. "Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions." Chemical Science 9, no. 45 (2018): 8528–34. http://dx.doi.org/10.1039/c8sc03570a.

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17

MUELLER, P., and J. MAREDA. "ChemInform Abstract: Bridgehead Reactivity in Solvolysis Reactions." ChemInform 22, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.199119309.

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18

Tsuji, Yutaka, and John P. Richard. "Reactions of ion-pair intermediates of solvolysis." Chemical Record 5, no. 2 (2005): 94–106. http://dx.doi.org/10.1002/tcr.20038.

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19

V., Jagannadham. "Substituent effects on the spontaneous cleavage of α-methylbenzylgem- dichlorides in aqueous solution". Journal of Indian Chemical Society Vol. 82, Aug 2005 (2005): 759–60. https://doi.org/10.5281/zenodo.5830280.

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Department of Chemistry, Osmania University, Hyderabad-500 007, India <em>E-mail</em> jagannadham1950@yahoo.com <em>Manuscript received 1 September 2004, revised 8 March 2005, accepted 6 May 2005</em> The solvolysis reactions of α-methylbenzyl-gem-dichlorides in water proceed by a stepwise mechanism through a-chloro-α-methylbenzyl carbocation intermediates, which are captured by water with a rate constant k<sub>s</sub>/s to give the corresponding acetophenones as the sole detectable products. 

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20

Lee, Choi Chuck, and Charles Y. Fiakpui. "Some isotopic scrambling studies with singly or doubly labeled triphenylvinyl bromide." Canadian Journal of Chemistry 63, no. 3 (1985): 681–84. http://dx.doi.org/10.1139/v85-112.

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The solvolysis of triphenyl[2-14C]vinyl bromide (1-Br-2-14C) in 70% HOAc – 30% H2O or in 2,2,2-trifluoroethanol (TFE) carried out in the presence of an excess of p-CH3C6H4SNa gave the triphenylvinyl p-tolyl thioether (1-STol) with a greatly decreased extent of scrambling of the 14C-label from C-2 to C-1 when compared with analogous reactions without the presence of the p-toluenethiolate anion. For example, the 1-STol product from the reaction of 1-Br-2-14C in 70% HOAc – p-CH3C6H4SNa showed only 0.5–0.9% scrambling, while previous studies on the reaction of 1-Br-2-14C in 70% HOAc – NaOAc gave 1

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21

Brandner, David G., Jacob S. Kruger, Nicholas E. Thornburg, et al. "Flow-through solvolysis enables production of native-like lignin from biomass." Green Chemistry 23, no. 15 (2021): 5437–41. http://dx.doi.org/10.1039/d1gc01591e.

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Flow-through solvolysis offers an opportunity to limit lignin condensation reactions that prevent isolation of native lignin in biomass processing, thus allowing for the study of intrinsic lignin properties and steady-state lignin depolymerization.

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22

Firmino, Thiago Diamond Reis, Jair J. Menegon, and José M. Riveros. "Gas-phase solvolysis type reactions of SiCl3+ cations." Química Nova 33, no. 10 (2010): 2098–102. http://dx.doi.org/10.1590/s0100-40422010001000018.

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23

KONDO, YOSHIKAZU, YOJI MITADERA, and SHIGEO NOZOE. "Oxindoles. V. Selective Solvolysis Reactions of Oxindole-Spirodimer." YAKUGAKU ZASSHI 105, no. 8 (1985): 724–29. http://dx.doi.org/10.1248/yakushi1947.105.8_724.

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24

Mclure, FI, RK Norris, and K. Wilson. "Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates." Australian Journal of Chemistry 40, no. 1 (1987): 49. http://dx.doi.org/10.1071/ch9870049.

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The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic , were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRNl process r

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25

Popov, Stasik, Brian Shao, Alex L. Bagdasarian, et al. "Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations." Science 361, no. 6400 (2018): 381–87. http://dx.doi.org/10.1126/science.aat5440.

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Vinyl carbocations have been the subject of extensive experimental and theoretical studies over the past five decades. Despite this long history in chemistry, the utility of vinyl cations in chemical synthesis has been limited, with most reactivity studies focusing on solvolysis reactions or intramolecular processes. Here we report synthetic and mechanistic studies of vinyl cations generated through silylium–weakly coordinating anion catalysis. We find that these reactive intermediates undergo mild intermolecular carbon-carbon bond–forming reactions, including carbon-hydrogen (C–H) insertion i

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26

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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27

Trilleras, Jorge, Alfredo Pérez-Gamboa, and Jairo Quiroga. "SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde." Molbank 2022, no. 3 (2022): M1426. http://dx.doi.org/10.3390/m1426.

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We report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to the influence of structural factors of the starting pyrimidine and a high concentration of alkoxide ions. This method allows the building of pyrimidine-based compound precursors of N-heterocyclic systems.

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28

Degeest, DJ, and PJ Steel. "Cyclometallated Compounds. IX. Reactions of 2-Benzoylpyridine With Rhodium(III) Trichloride." Australian Journal of Chemistry 48, no. 9 (1995): 1573. http://dx.doi.org/10.1071/ch9951573.

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X-Ray crystallography and n.m.r. spectroscopy have been used to study the products of reactions between rhodium(III) trichloride and 2-benzoylpyridine under various reaction conditions. X-Ray crystal structures have shown that the initial product of reaction in refluxing ethanol is a centrosymmetric isomer, as previously proposed, but that this undergoes aqueous hydrolysis to a C2-symmetric isomer, rather than the previously proposed C2v isomer. Reaction in refluxing 2-methoxyethanol produces an unusual complex with one C-N cyclometallated ligand and one N-O coordinated ligand. In Me2SO, the n

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29

Fowless, AD, GA Lawrance, DR Stranks, TR Sullivan, and N. Vanderhoek. "The Effect of Pressure on the Anation of Diaquabis(ethane-1,2-diamine)cobalt(III) by Selenate and Sulfate, and on the Isomerization of the trans-Aquabis(ethane-1,2-diamine)(hydrogenselenito)cobalt(III) Ion." Australian Journal of Chemistry 41, no. 9 (1988): 1263. http://dx.doi.org/10.1071/ch9881263.

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The reversible nucleophilic substitution of cis-[Co(en)2(OH2)2]3+ (en = ethane-1,2-diamine) by sulfate and selenate at pH 2.0 was studied at elevated pressure, and activation volumes (ΔV‡) for anation and solvolysis were determined. The ΔV‡ values for anation by sulfate and selenate were +8.3�0.5 and +8.5�0.4 cm3 mol-1 respectively, whereas solvolysis of sulfato and selenato complexes cis -[Co(en)2(OH2)(XO4)]+ gave ΔV‡ values of -2.2�0.4 and -3.3�0.7 cm3 mol-1 respectively. The trans → cis [Co(en)2(OH2)(OSeO2H)]2+ isomerization studied at pH 1.0 and elevated pressure yielded ΔV‡ + 7.2�0.4 cm3

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30

SHIMIZU, N. "ChemInform Abstract: Silicon Effects in Solvolysis and Related Reactions." ChemInform 25, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199425281.

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31

Fischer, Alfred, George N. Henderson, and Trevor A. Smyth. "Reactions of the 1-hydroxy-1,4-dimethylcyclohexadienyl cation, an intermediate in the solvolysis of 1,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-ol." Canadian Journal of Chemistry 64, no. 6 (1986): 1093–101. http://dx.doi.org/10.1139/v86-184.

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Solvolysis of 1,4-dimethyl-4-nitrocyclohexa-2,5-dien-1-ol in mixed aqueous organic solvents gives the diastereomers of 1,4-dimethylcyclohexa-2,5-diene-1,4-diol, 1,4-dimethylcyclohexa-3,5-diene-1,2-diol, 2-nitro-p-xylene, 2,4-dimethylphenol (all derived from the title cation, itself formed by ionization of the nitro group as nitrite), and 2,5-dimethylphenol. In aqueous methanol the diastereomers of 4-methoxy-1,4-dimethylcyclohexa-2,5-dienol are also obtained. Significant yields of 2,5-dimethylphenol are only obtained on the acid-catalysed further reaction of the dienediol (or the methoxydienol)

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32

Hanessian, Stephen, and René Roy. "Chemistry of spectinomycin: its total synthesis, stereocontrolled rearrangement, and analogs." Canadian Journal of Chemistry 63, no. 1 (1985): 163–72. http://dx.doi.org/10.1139/v85-026.

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The total stereocontrolled synthesis of the antibiotic spectinomycin is described, based on the regiospecific functionalization and manipulation of appropriate starting materials. The tertiary ketol rearrangement of the antibiotic and its derivatives was studied and the stereochemical identity of spectinoic acid was established by chemical correlation. Dihydrospectinomycin derivatives undergo unusual solvolysis reactions.

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33

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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34

Forbes, Rowena M., and H. Maskill. "Sulphonyl transfer reactions: solvolysis of arenesulphonyl chlorides in aqueous trifluoroethanol." Journal of the Chemical Society, Chemical Communications, no. 13 (1991): 854. http://dx.doi.org/10.1039/c39910000854.

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35

Chandrasena, R. Esala P., David Aebisher, and Martin Newcomb. "Products from solvolysis reactions that form (2-phenylcyclopropyl)carbinyl cations." Journal of Physical Organic Chemistry 18, no. 9 (2005): 974–77. http://dx.doi.org/10.1002/poc.951.

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36

Schneider, Hans-Jörg, and Günter Schmidt. "Solvolysis reactions and force field calculations with epimeric cyclohexane derivatives." Chemische Berichte 119, no. 1 (1986): 65–73. http://dx.doi.org/10.1002/cber.19861190107.

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37

Meng, Qingshui, Baoan Du, and Alf Thibblin. "Mechanisms of elimination and substitution reactions. Spontaneous solvolysis reactions via carbanion and carbocation intermediates." Journal of Physical Organic Chemistry 12, no. 2 (1999): 116–22. http://dx.doi.org/10.1002/(sici)1099-1395(199902)12:2<116::aid-poc102>3.0.co;2-8.

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38

Kurzer, Frederick, and C. Richard Duffner. "Diisophorone and Related Compounds, Part 27 [1] Nucleophilic Reactions of 1-Halogenodiisophoranes." Zeitschrift für Naturforschung B 45, no. 9 (1990): 1314–23. http://dx.doi.org/10.1515/znb-1990-0915.

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The action of nucleophiles on 1-halogenodiisophoranes, obtained by several methods from the corresponding 1-hydroxy or 1-alkoxy compounds, replaces their bridgehead 1-halogen by hydroxy, alkoxy or acetoxy groups. The semiquantitative results show that the high solvolysis and hydrolysis rates of the 1-halogenodiisophor-2(7)-en-3-ones contrast markedly with the low reactivities of their 3-deketo analogues. Perchloric acid-catalyzed acetylation of diisophor-2(7)-en-1-ol-3-ones yields, by enolisation of the 3-keto-group, 1,3-diacetoxydiisophora-2,7-dienes in addition to the usual 1-monoacetates.

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39

Kühn-Velten, Jobst, Matthias Bodenbinder, Raimund Bröchler, Gerhard Hägele, and Friedhelm Aubke. "A 19F nuclear magnetic resonance study of the conjugate BrønstedLewis superacid HSO3FSbF5. Part II." Canadian Journal of Chemistry 80, no. 9 (2002): 1265–77. http://dx.doi.org/10.1139/v02-139.

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Solutions of SbF5 in HSO3F with xSbF5 = 0.012 to 0.405 are studied by 500 MHz 1H NMR (299 K) and 471 MHz 19F NMR (213250 K), using NMR tubes fitted with fluoropolymer lining. The initial process during dissolution is the fast solvolysis of monomeric SbF5 in HSO3F according to SbF5 + nHSO3F [Formula: see text] SbF5 n(SO3F)n + nHF (n = 1, 2). All HF formed during solvolysis will no longer be removed by reaction with glass, but will remain in the superacid system. Besides participation in the fast formation of various fluoro-fluorosulfato anions [SbF6 n(SO3F)n] (n = 0, 1, 2) and acidium ion

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40

Kochly, Elizabeth D., Susan Citrak, Nelius Gathondu, and Gabriella Amberchan. "Effect of ionic liquids in unimolecular solvolysis reactions involving carbocationic intermediates." Tetrahedron Letters 55, no. 52 (2014): 7181–85. http://dx.doi.org/10.1016/j.tetlet.2014.10.145.

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41

Graham, William H. "Solvolysis reactions of bis(difluoramino)ethylenes: a route to nitrenium ions." Journal of Fluorine Chemistry 48, no. 3 (1990): 319–30. http://dx.doi.org/10.1016/s0022-1139(00)80216-x.

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42

Roe, Caroline, Elizabeth J. Sandoe, and G. Richard Stephenson. "Solvolysis reactions at the 13th carbon of 1-aryl organoiron complexes." Tetrahedron Letters 51, no. 4 (2010): 591–95. http://dx.doi.org/10.1016/j.tetlet.2009.11.052.

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43

Brochier Salon, Marie-Christine, Michel Bardet, and Mohamed Naceur Belgacem. "Solvolysis–hydrolysis of N-bearing alkoxysilanes: Reactions studied with 29Si NMR." Silicon Chemistry 3, no. 6 (2008): 335–50. http://dx.doi.org/10.1007/s11201-008-9036-4.

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44

Xu, Zhao-Bing, and Jin Qu. "Hot Water-Promoted SN1 Solvolysis Reactions of Allylic and Benzylic Alcohols." Chemistry - A European Journal 19, no. 1 (2012): 314–23. http://dx.doi.org/10.1002/chem.201202886.

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45

Harsanyi, MC, та RK Norris. "Substitution Reactions of α-Alkyl 4- and 5-Nitropyrrol-2-ylmethyl Derivatives". Australian Journal of Chemistry 40, № 12 (1987): 2063. http://dx.doi.org/10.1071/ch9872063.

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The α-t-butyl 4- and 5-nitropyrrol-2-yl chlorides (5b) and (6b) react with azide, thiocyanate and p- toluenethiolate ions in dimethylformamide through cationic species in an SN 1-type process, rather than by the SRNl or SN(AEAE) processes, by which their analogues in the benzene, furan or thiophen systems react. These reactions are so facile that they take place in the aqueous dimethylformamide solutions produced during the workup of reaction mixtures. Solvolysis of (5b) or (6b) in methanol produces high yields of the corresponding methyl ethers (5f) and (6f) The chloride (6b) reacts with meth

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46

Salmar, Siim, Jaak Järv, Tiina Tenno, and Ants Tuulmets. "Role of water in determining organic reactivity in aqueous binary solvents." Open Chemistry 10, no. 5 (2012): 1600–1608. http://dx.doi.org/10.2478/s11532-012-0080-8.

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AbstractKinetic data for organic reactions in various binary water-organic solvent mixtures were collected and quantitatively analysed in terms of linear-free-energy relationships by using tert-butyl chloride (2-chloro-2-methylpropane) solvolysis as the reference system. Linear similarity plots for these kinetic data were determined for solvent systems ranging from pure water mixtures up to considerable amount of cosolvent, and 161 similarity coefficients were calculated from slopes of these plots. The existence of these linear plots demonstrated that the solvent effects are of some common nat

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47

Bentley, T. William. "Role of solvent nucleophilicity in excess-acidity plots for equilibria in sulfuric acid – water mixtures." Canadian Journal of Chemistry 86, no. 4 (2008): 277–80. http://dx.doi.org/10.1139/v08-003.

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For protonation of a base B to give BH+ and for reaction of carbocations R+ with water to give ROH in a range of sulfuric acid – water mixtures, slopes of excess-acidity plots of equilibrium data are discussed. Formal connections between the excess-acidity approach and the Grunwald–Winstein (GW) and extended GW equations, noted previously by Bagno et al., are evaluated. It is proposed that a major factor is variations in the solvent dependence of the rates of reactions of the cations (BH+ or R+) with water in the sulfuric acid – water mixtures. Rates of reactions of more stable cations (e.g.,

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48

Saunders, James, Chris Adamson, Yumeela Ganga-Sah, Andrew R. Lewis, and Andrew J. Bennet. "Rearrangement and nucleophilic trapping of bicyclo[4.1.0]hept-2-yl derived nonclassical bicyclobutenium ions." Canadian Journal of Chemistry 96, no. 2 (2018): 235–40. http://dx.doi.org/10.1139/cjc-2017-0569.

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Here we describe the synthesis of two specifically labelled 13C isotopologues of cis-2-(4-nitrophenoxy)bicyclo[4.1.0]heptane and their solvolysis reactions in trifluoroethanol. By using one- and two-dimensional 1H- and 13C-NMR spectroscopy, we characterized the pathways for the rearrangement of these isotopologues to give 13C-labelled 4-(2,2,2-trifluoroethoxy)cycloheptene. We show that the initially formed cationic intermediate undergoes a degenerate rearrangement, which does not reach equilibrium before nucleophilic capture of the cation. Moreover, we show that the nonclassical carbocation, c

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49

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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50

Verma, Pramod Kumar, Abhinanadan Makhal, Rajib Kumar Mitra, and Samir Kumar Pal. "Role of solvation dynamics in the kinetics of solvolysis reactions in microreactors." Physical Chemistry Chemical Physics 11, no. 38 (2009): 8467. http://dx.doi.org/10.1039/b905573h.

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