Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors
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| Format: | Artículo científico |
| Language: | en |
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Sociedad Química de México
2005
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| _version_ | 1876446810119077888 |
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| author | Aarón Flores Figueroa |
| author_facet | Aarón Flores Figueroa |
| contents | Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors Aarón Flores Figueroa Víctor Arista-M Daniel Talancón Sánchez Ivan Castillo Multidisciplinaria (Ciencias Naturales y Exactas) thiols thiophenols bulky thiols ray structure thiocarbamates A series of thiophenols with different ortho-substituents, 2,4-dimethylthiophenol, 2-tert-butyl-4-methylthiophenol, and 2-(1-adamantyl)-4-methylthiophenol, which display varying degrees ofsteric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonationof the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,Ndimethylthiocarbamoylchloride, to obtain the O-arylthiocarbamates. Thermolysis of the lattercompounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally,reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed theisolation of the thiophenols. All products were characterized by spectroscopic techniques, and in thecase of some of the thiocarbamates the solid state structures were determined by single-crystal X-raydiffraction. 2005 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47549213 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.49 |
| format | Artículo científico |
| id | redalyc_47549213 |
| institution | Redalyc |
| language | en |
| publishDate | 2005 |
| publisher | Sociedad Química de México |
| spellingShingle | Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors Aarón Flores Figueroa Multidisciplinaria (Ciencias Naturales y Exactas) thiols thiophenols bulky thiols ray structure thiocarbamates Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors Aarón Flores Figueroa Víctor Arista-M Daniel Talancón Sánchez Ivan Castillo Multidisciplinaria (Ciencias Naturales y Exactas) thiols thiophenols bulky thiols ray structure thiocarbamates A series of thiophenols with different ortho-substituents, 2,4-dimethylthiophenol, 2-tert-butyl-4-methylthiophenol, and 2-(1-adamantyl)-4-methylthiophenol, which display varying degrees ofsteric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonationof the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,Ndimethylthiocarbamoylchloride, to obtain the O-arylthiocarbamates. Thermolysis of the lattercompounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally,reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed theisolation of the thiophenols. All products were characterized by spectroscopic techniques, and in thecase of some of the thiocarbamates the solid state structures were determined by single-crystal X-raydiffraction. 2005 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47549213 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.49 |
| title | Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) thiols thiophenols bulky thiols ray structure thiocarbamates |
| url | https://www.redalyc.org/articulo.oa?id=47549213 |