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.
10.1021/jo001737+
The research focuses on the synthesis of (-)-delobanone, a sesquiterpene, using a novel approach that involves the preparation of alkenyl cyclopropane 2 from the Sharpless-derived epoxide 1. The key reactants include geraniol, which undergoes Sharpless epoxidation to form an epoxide, followed by sulfonylation to produce benzenesulfonate 11. This is then reacted with lithioacetonitrile to yield nitrile 9, which is further transformed into aldehyde 8 through a DIBAL-H reduction. The aldehyde is converted into an alkenyl cyclopropane 2 via a Wittig reaction. The final step involves the irradiation of 2 in the presence of Fe(CO)5 under a CO atmosphere to achieve the ring expansion, resulting in (-)-delobanone 3. Throughout the synthesis, various analytical techniques were employed, including NMR, IR, MS, and optical rotation measurements, to monitor the progress and confirm the structures of the intermediates and final product. The research also discusses the potential challenges and the successful optimization of the reaction conditions to achieve high yields and selectivity.
10.1039/c39860000784
The research explores a new route to synthesizing indoles through the deoxygenation of ortho-nitrostyrenes using carbon monoxide and metal carbonyl catalysts. The purpose is to develop a more selective and efficient method for constructing the indole nucleus under non-acidic conditions, which is of significant academic and industrial interest. Key chemicals used include Fe(CO)5, Ru3(CO)12, and Rh6(CO)16 as catalysts, along with various ortho-nitrostyrene substrates prepared via a modified Wittig reaction. The study found that Fe(CO)5 was the most selective catalyst, yielding primarily indoles with some side products like amines and quinolones. The method offers advantages over traditional deoxygenation methods, such as better selectivity and a simpler work-up procedure. The research also isolated a non-catalytically active rhodium complex during the synthesis, providing insights into the catalytic mechanism.
10.1055/s-2002-32962
The research aims to develop a more efficient and general procedure for the conversion of N-allylamides to enamides using iron pentacarbonyl (Fe(CO)5) as a catalyst. The study demonstrates that the isomerization of various N-allylamides in the presence of Fe(CO)5 can yield the corresponding enamides with high efficiency, up to 95% yield, and is compatible with a variety of functional groups, including protected amino and hydroxy groups. The process is advantageous due to the inexpensive and readily available catalyst, and the mild reaction conditions that are suitable for the synthesis of highly functionalized molecules. The research concludes that this method provides a competitive alternative to known methods for the preparation of tertiary enamides and could be valuable for the removal of N-allyl protecting groups from amides.
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