10.1016/S0022-328X(00)96083-2
The study explores the application of free radicals in the catalytic synthesis of carbon monoxide derivatives, focusing on the reaction of carbon monoxide with organomagnesium compounds in the presence of various carbonyl compounds in tetrahydrofuran. The main product of these reactions was tetrahydrofuranyl-2-ethyl ketone, suggesting a radical mechanism. The reactions were found to be complex, yielding over ten products, including ketones, tertiary alcohols, and hydrocarbons. The study also discusses the potential for other radical sources to facilitate similar reactions, opening new avenues for organic synthesis.
10.1246/bcsj.68.1401
The research investigates the reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and secondary amines. The purpose of the study was to explore the transformation of sulfoxides into sulfides, dithioacetals, and vinyl sulfides, which are important intermediates in organic synthesis. The researchers found that diaryl sulfoxides were reduced to diaryl sulfides, sulfoxides bearing α-hydrogens yielded dithioacetals, and those with both α- and β-hydrogens produced vinyl sulfides along with dithioacetals. The conclusions of the study highlight the utility of magnesium amides as reagents for the eliminative deoxygenation of sulfoxides, providing a new method for the preparation of sulfides, dithioacetals, and vinyl sulfides.
10.1055/s-0034-1380748
The research aims to develop a method for synthesizing 2-(benzylthio)-4-(trifluoromethyl)thiazole-5-carboxylates using S-benzylisothiouronium halides as thiol equivalents. The purpose is to create a practical and safe synthetic route for these compounds, which are important in pharmaceuticals and agrochemicals, while avoiding the use of malodorous and toxic benzylthiols. The key chemicals used include 2-bromothiazole, various S-benzylisothiouronium halides, and ethylmagnesium bromide. The method involves a nucleophilic aromatic substitution reaction monitored by 19F NMR spectroscopy due to the presence of a trifluoromethyl group. The study concludes that the S-benzylisothiouronium halides are effective thiol surrogates, allowing for the synthesis of the target compounds in high yields (typically around 80%) and with good scalability. The method is also extendable to a one-pot process that includes ester hydrolysis, further simplifying the synthesis.
10.1021/jo01225a005
The study focuses on the synthesis and analysis of certain benzanthracene derivatives with potential estrogenic and carcinogenic properties. The researchers synthesized various 9,10-dialkyl-9,10-dihydroxy-9,10-dihydro-1,2-benzanthracenes and related compounds, starting from 1,2-benzanthraquinone and 5-phenyl-1,2-benzanthraquinone. They used Grignard reagents, such as methylmagnesium iodide, ethylmagnesium bromide, and n-propylmagnesium bromide, to introduce different alkyl groups into the benzanthracene structure. The synthesized compounds were then tested for their ability to induce oestrus in ovarietomized mice, revealing that some of them, particularly those with ethyl and n-propyl groups, exhibited significant estrogenic activity. Additionally, the study explored the relationship between chemical structure and both estrogenic and carcinogenic properties, aiming to understand how modifications to the benzanthracene core affect these biological activities.