Kinetics and mechanism of oxidation of substituted phenyl methyl sulphides by n-bromoacetamide

Perumal, S.; Alagumalai, Sakkiah; Selvaraj, S.; Arumugam, N.

doi:10.1016/s0040-4020(01)82068-8

Cited by 27 publications

(11 citation statements)

References 16 publications

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“…by chloramine-T(4.25), 29 bromine (3.2) 30 and N-bromoacetamide (3.75). 31 In the oxidation by N-chloroacetamide (NCA) 32 the values of the field (I) and resonance ( + R), at 298 K are 1.3 and 1.7 respectively.…”

Section: Aryl Methyl Sulfidesmentioning

confidence: 99%

Oxidation of Organic Sulfides by Quinolinium Chlorochromate: A Kinetic and Mechanistic Approach

Sharma¹,

Rathi²,

Sharma³

et al. 2017

ECB

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The oxidation of organic sulfides by quinolinium chlorochromate (QCC) resulted the formation of the corresponding organic sulfoxides. These reactions are first order ones with respect to QCC. A Michaelis-Menten type kinetics was observed with respect to the reactants. The reaction is catalyzed by p-toluene sulfonic acid (TsOH). The oxidation was studied in nineteen different organic solvents. An analysis of the solvent effect on Swain's equation showed that the both cation-and anion-solvating powers of the solvents play important roles. The correlation analyses of the rate of oxidation of thirty-four sulfides were done in terms of various single and multiparametric equations. In the reactions of aryl methyl sulfides, the best correlation could be obtained with Charton's LDR and LDRS equations. The oxidation reactions of alkyl phenyl sulfides exhibited an excellent correlation in terms of Pavelich-Taft equation. The negative values of polar reaction constants indicate an electron-deficient sulfur center in the rate-determining step. The proposed reaction mechanism involves the formation of a sulphenium cation intermediate in a slow step * Corresponding AuthorsPhone: +91 94144-10900 E-Mail: drpkvs27@yahoo.com [a]

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Section: Aryl Methyl Sulfidesmentioning

confidence: 99%

Oxidation of Organic Sulfides by Quinolinium Chlorochromate: A Kinetic and Mechanistic Approach

Sharma¹,

Rathi²,

Sharma³

et al. 2017

ECB

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“…175 Aqueous solutions of chlorine dioxide can be used for the chemoselective synthesis of g-oxo sulfoxides in moderate-to-good yield. 176 Active halogen sources such as NCS or N-bromosuccinimide (NBS), 177 N-chloroacetamide (NCA), 178 chloramines, 179 and bromamines 180 are well-known reagents for the oxidation of sulfides to sulfoxides. More recently, 4,4-dibromo-3-methylpyrazol-5-one in acetic acid, 181 TCCA 182 in acetonitrile-dichloromethane-pyridine, and NBS/b-cyclodextrin 183 in water mixture have been reported to selectively oxidize sulfides to sulfoxides in good-to-high yield.…”

Section: Scheme 13mentioning

confidence: 99%

7.28 Oxidation of Sulfur, Selenium, and Tellurium

Lattanzi

2014

Comprehensive Organic Synthesis II

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“…Large negative reaction constants were exhibited by oxidations involving formation of halogeno-sulfonium cations, e.g. by chloramine-T ( À 4.25) [35], bromine ( À 3.2) [36] and N-bromoacetamide ( À 3.75) [37]. In the oxidation by N-chloroacetamide (NCA) [38] the values of field (r I ) and resonance (r þ R ), at 298 K are À 1.3 and À 1.7 respectively.…”

Section: Aryl Methyl Sulfidesmentioning

confidence: 99%

Oxidation of Some Organic Sulfides by Benzyltrimethylammonium Chlorobromate: A Kinetic and Mechanistic Approach

Tiwari

Meena

Daiya

et al. 2012

Progress in Reaction Kinetics and Mechanism

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The oxidation of 34 sulfides by benzyltrimethylammonium chlorobromate (BTMACB) resulted in formation of the corresponding sulfoxides. The reaction is first order with respect to both BTMACB and the sulfide. The solvent composition effect indicated that the rate of reaction increases with increase in the polarity of the medium. The reaction failed to induce the polymerization of acrylonitrile. There is no effect of added benzyltrimethylammonium chloride or potassium bromide. Chlorobromate ion is postulated as the reactive oxidizing species. The rates of oxidation of meta-and para-substituted phenyl methyl sulfides were correlated with Charton's LDR equation. The rates of oxidation of the ortho-compounds showed excellent correlation with the LDRS equation. The oxidation of meta-compounds exhibited a greater dependence on the field effect. The reaction is subject to steric inhibition when an ortho-substituent is present. The oxidation of alkyl phenyl sulfides is subject to both polar and steric effects of the alkyl groups. The polar reaction constants are negative, indicating an electrondeficient sulfur centre in the rate-determining step. A mechanism has been proposed involving formation of a halogenosulfonium cation in the slow step.

show abstract

Kinetics and mechanism of oxidation of substituted phenyl methyl sulphides by n-bromoacetamide

Cited by 27 publications

References 16 publications

Oxidation of Organic Sulfides by Quinolinium Chlorochromate: A Kinetic and Mechanistic Approach

Oxidation of Organic Sulfides by Quinolinium Chlorochromate: A Kinetic and Mechanistic Approach

7.28 Oxidation of Sulfur, Selenium, and Tellurium

Oxidation of Some Organic Sulfides by Benzyltrimethylammonium Chlorobromate: A Kinetic and Mechanistic Approach

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