67382-72-3Relevant academic research and scientific papers
Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide
Holmes, Brian T.,Snow, Arthur W.
, p. 12339 - 12342 (2007/10/03)
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.
Conversion of alcohols to thiols via tosylate intermediates
Snow, Arthur W.,Foos, Edward E.
, p. 509 - 512 (2007/10/03)
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.
Acid-Catalyzed Solvolysis of N-Sulfonyl- and N-Acyl-O-arylhydroxylamines. Phenoxenium Ions
Endo, Yasuyuki,Shudo, Koichi,Okamoto, Toshihiko
, p. 6393 - 6397 (2007/10/02)
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.
