The Organic Reactions and Synthesis based on the Utilization of Carbon Monoxide

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1. Synthesis utilization reducing ability of carbon monoxide, - Using CO/H_2O/Se reaction system-(1) In the reductive dibromination of vic-dibromoalkanes with CO and H_2O in the presence of a catalytic amount of Se, vic-dibromoalkanes were converted to the corresponding alkanes in good yields and stereospecific.(2) The selective generation of tertiary amine salts of hydrogen selenide and diselenide has been achived by controlling the reaction conditions. Diorganylselenides and diorganyldiselenides were synthesized in good yields with perfect selectivity.(3) Phenyl substituted alpha- and beta-diketones were reduced to corresponding aromatic ketones in moderate to good yields.2. Utilization of carbon monoxide as a useful agentas for introducing carbonyl functions into organic molecules.(1) Treatment of 1, 1- or 1, 2-diphenylalkanes in benzene with AlCl_3-HCl formed the red-oil involving a phenylalkylcarbocations. When carbon monoxide was introduced to the red-oil, the phenylalkylcarbocations reacted with carbon monoxide to give 2-disubstituted-1-indanones via cyclization of the resulting acylcation.(2) 1-adamantanecarboxaldehyde was synthesized by the AlI_3-catalyzed reaction of adamantane with CO in CH_2Cl_2 at < 25ﾟC