1963
DOI: 10.1021/jo01045a076
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Alkylmercaptophenols by Sulfenylation of Phenols

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Cited by 36 publications
(12 citation statements)
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“…IR spectra were obtained as KBr pellets on a Bruker Vector 22 instrument. 1 The ligand was sinthesized by a Mannich reaction of 2-(methylthio)-p-cresol [21] with bis(2-pyridylmethyl) amine [22], paraformaldehyde, and 2-(methylthio)-p-cresol in 57% yield, as described previously [2]. 1 CuCl 2 (0.27 g, 2 mmol) was added to a solution of the ligand HSL (2 mmol) and triethylamine (2 mmol) in methanol (10 mL), and the mixture was refluxed for 60 min.…”
Section: Methodsmentioning
confidence: 99%
“…IR spectra were obtained as KBr pellets on a Bruker Vector 22 instrument. 1 The ligand was sinthesized by a Mannich reaction of 2-(methylthio)-p-cresol [21] with bis(2-pyridylmethyl) amine [22], paraformaldehyde, and 2-(methylthio)-p-cresol in 57% yield, as described previously [2]. 1 CuCl 2 (0.27 g, 2 mmol) was added to a solution of the ligand HSL (2 mmol) and triethylamine (2 mmol) in methanol (10 mL), and the mixture was refluxed for 60 min.…”
Section: Methodsmentioning
confidence: 99%
“…Synthesis and Characterization --DMP was synthesized by sulfenylation of 3,5-dimethylphenol using dimethyl disulfide under acidic conditions. 30) A mixture of 3,5-dimethylphenol (6.1 g, 50 mmol) and sulfuric acid (0.2 g) was heated to 170 • C and then cooled 155 • C. Dimethyl disulfide (4.7 g, 50 mmol) was added over a period of 30 min, and the mixture was heated at 155 • C for 5 hr. The charcoal brown product was then fractionally distilled under aspirator pressure; fractions between 127 and 144 • C, which were collected and combined, yielded 0.28 g. To obtain pure DMP, the fraction was purified with HPLC (Shimadzu LC-20AD HPLC system; Shimadzu Corporation, Kyoto, Japan).…”
Section: Methodsmentioning
confidence: 99%
“…No sulfanylation occurred when the resin-bound 2-aminothiazoles 11 were treated with disulfides in the absence of iodine, and it is therefore assumed that the electrophilic sulfanylating intermediates generated in situ must be Complexes between disulfides and Lewis acids, [22,23,35] Brønsted acids, [36,37] or iodine [24] have been suggested as the reactive electrophilic intermediates in several substitution and addition reactions. Spectrophotometric studies furthermore also indicated the existence of 1:1 charge-transfer complexes between disulfides and iodine in solution.…”
Section: Mechanistic Considerationsmentioning
confidence: 99%