Oxidations of aromatic sulfides promoted by the phthalimide N-oxyl radical (PINO)

IF 2.1 3区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Marika Di Berto Mancini , Alessandro Tabussi , Marianna Bernardini , Osvaldo Lanzalunga
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引用次数: 1

Abstract

The oxidation of a series of alkyl aryl sulfides promoted by the phthalimide N-oxyl radical (PINO) has been investigated by kinetic and product analysis. Sulfoxides are formed as major reaction products in the oxidation of thioanisoles and benzyl phenyl sulfides. The observation of fragmentation products in the oxidation of 2-phenyl-2-propyl phenyl sulfide and diphenylmethyl phenyl sulfide indicates that the reaction involves an initial electron transfer reaction from the sulfide to PINO with the formation of aryl sulfide radical cations and the anion PINO-. Combination of the species then leads to a radical adduct precursor of sulfoxides while the rapid C–S cleavage occurs with aryl sulfide radical cations that can form the stable 2-phenyl-2-propyl or diphenylmethyl carbocation.

邻苯二甲酸亚胺n -氧自由基(PINO)对芳香族硫化物的氧化作用
通过动力学和产物分析研究了邻苯二甲酸亚胺n -氧自由基(PINO)对一系列烷基芳基硫化物的氧化作用。亚砜是硫苯甲醚和苯基苯基硫化物氧化的主要反应产物。对2-苯基-2-丙基苯基硫化物和二苯基甲基苯基硫化物氧化过程中碎裂产物的观察表明,该反应涉及一个由硫化物到PINO的初始电子转移反应,并形成芳基硫化物自由基阳离子和阴离子PINO-。这两种物质的结合会导致亚砜的自由基加合前体,而芳基硫化物自由基阳离子会发生快速的C-S裂解,形成稳定的2-苯基-2-丙基或二苯基甲基碳正离子。图形抽象
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来源期刊
Journal of Sulfur Chemistry
Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
4.10
自引率
9.10%
发文量
38
审稿时长
6-12 weeks
期刊介绍: The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.
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