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- W2308361982 abstract "S-methylation of a bituminous coal using {sup 13}C-enriched methyl iodide in the presence of silver tetrafluoroborate produces significant quantities of trimethylsulfonium ion as determined by {sup 13}C NMR. This result suggests that carbon-sulfur bonds in coal are being cleaved. In an effort to determine the types of structures in coal responsible for this ion, a series of model substituted dibenzyl sulfides were S-methylated. The substrates included 4,4{prime}dimethoxydibenzylsulfide (1), 4,4{prime}dimethyldibenzylsulfide (2), dibenzylsulfide (3), 4,4{prime}dichlorodibenzylsufide (4). All substrates are cleaved to varying degrees in refluxing DCE (83{degrees}C) to produce a mixture of methyldibenzyl-, dimethylbenzyl- and trimethylsulfonium ions. The relative amounts of these ions depends on the substituent, with the degree of C-S bond cleavage increasing with the electron-donating ability of the substituent in the order (1) > (2) > (3) > (4). A mechanism is proposed consistent with this substituent effect which involves an intermediate benzyl carbocation - sulfide ion-dipole complex." @default.
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- W2308361982 date "1996-10-01" @default.
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- W2308361982 title "Cleavage of carbon-sulfur bonds in coal and substituted dibenzyl sulfides" @default.
- W2308361982 hasPublicationYear "1996" @default.
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