- Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
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A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols.
- Holmes, Brian T.,Snow, Arthur W.
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p. 12339 - 12342
(2007/10/03)
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- Conversion of alcohols to thiols via tosylate intermediates
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High yielding syntheses of mercapto terminated mono-disperse dimer, trimer, and tetramer ethyleneoxide oligomers and of p-hydroxyphenethyl thiol via an alcohol-tosylate-thiol route are reported. Comparisons are made with the more conventional alcohol-bromide-thiol route.
- Snow, Arthur W.,Foos, Edward E.
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p. 509 - 512
(2007/10/03)
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- Acid-Catalyzed Solvolysis of N-Sulfonyl- and N-Acyl-O-arylhydroxylamines. Phenoxenium Ions
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The acid-catalyzed reaction of N-acyl- and N-sulfonyl-O-arylhydroxylamines with benzene proceeded quite smoothly to give 2- and 4-hydroxybiphenyls.The results of product analysis, the orientation of the reaction, and the effects of substituents on the nitrogen atom and on the phenyl ring suggested a mechanism that involves a phenoxenium ion.The phenoxenium ion was trapped by benzene and other various nucleophiles.
- Endo, Yasuyuki,Shudo, Koichi,Okamoto, Toshihiko
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p. 6393 - 6397
(2007/10/02)
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