Synthesis of 2,4-disubstituted thiophenols and solid state structures of thiocarbamate precursors

Journal of the Brazilian Chemical Society

Universidad Nacional Autónoma de México, México, México¹  Flores-Figueroa, Aarón¹  Arista-M., Víctor¹  Talancón-Sánchez, Daniel¹  Castillo, Ivan¹ 

关键词: thiols;    thiophenols;    thiocarbamates;    bulky thiols;    X-ray structure;   

DOI  :  10.1590/S0103-50532005000300013

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

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 of steric hindrance on the 2-position, was prepared from the corresponding phenols. Initial deprotonation of the phenols was achieved with NaH in dimethoxyethane, followed by treatment with N,N-dimethylthiocarbamoyl chloride, to obtain the O-arylthiocarbamates. Thermolysis of the latter compounds resulted in rearrangement, which yields the desired S-arylthiocarbamates. Finally, reduction of the S-arylthiocarbamates with LiAlH4 in THF, followed by acidic workup, allowed the isolation of the thiophenols. All products were characterized by spectroscopic techniques, and in the case of some of the thiocarbamates the solid state structures were determined by single-crystal X-ray diffraction.

【 授权许可】

Unknown