Synthesis of 2,4-Disubstituted Thiophenols and Solid State Structures of Thiocarbamate Precursors
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 phe...
| Authors: | , , , |
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| Format: | article |
| Status: | Published version |
| Publication Date: | 2005 |
| Country: | México |
| Institution: | Universidad Nacional Autónoma de México |
| Repository: | Redalyc-UNAM |
| OAI Identifier: | oai:redalyc.org:47549213 |
| Online Access: | https://www.redalyc.org/articulo.oa?id=47549213 |
| Access Level: | Open access |
| Keyword: | Química thiols thiophenols bulky thiols ray structure thiocarbamates |
| Summary: | 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. |
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